[ CAS No. 27258-32-8 ] {[proInfo.proName]}

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Quality Control of [ 27258-32-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27258-32-8 ]

SDS Specification

Alternatived Products of [ 27258-32-8 ]

Product Details of [ 27258-32-8 ]

CAS No. :	27258-32-8	MDL No. :	MFCD03419800
Formula :	C₅H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUYJEYSRBCLJIZ-UHFFFAOYSA-N
M.W :	110.11	Pubchem ID :	7026090
Synonyms :

Calculated chemistry of [ 27258-32-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	28.88
TPSA :	34.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.75
Log Po/w (XLOGP3) :	0.03
Log Po/w (WLOGP) :	0.23
Log Po/w (MLOGP) :	-0.63
Log Po/w (SILICOS-IT) :	0.5
Consensus Log Po/w :	0.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	12.7 mg/ml ; 0.115 mol/l
Class :	Very soluble
Log S (Ali) :	-0.32
Solubility :	53.3 mg/ml ; 0.484 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.68
Solubility :	22.8 mg/ml ; 0.207 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.04

Safety of [ 27258-32-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 27258-32-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 27258-32-8 ]
Downstream synthetic route of [ 27258-32-8 ]

[ 27258-32-8 ] Synthesis Path-Upstream 1~6

1
[ 67751-23-9 ]
[ 60-34-4 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide In water at 20℃;	methyl hydrazine (24 cm3, 19.5 g, 0.423 mol) was added dropwise to a solution of 17.0 g NaOH (0.423 mol) in 225 cm3 H2O upon cooling. Compound 16 (73.3 g,0.423 mol) was then added dropwise at rt, and the mixture was stirred overnight. Aq. HCl (36 percent, 28.2 g, 0.278 mol) was added upon cooling, the reaction mixture was stirred at rt for 1 h, and then extracted with CH2Cl2 (4 9 100 cm3). The combined organic phases were dried over Na2SO4, and the solvent was evaporated under reduced pressure. The residue was dissolved in 420 cm3 1 M aq. HCl and stirred at rt for 3 h. Then 10 percent aq K2CO3 was added to adjust pH = 10, and the mixture was extracted with CH2Cl2 (3 9 200 cm3). The organic layer was dried in vacuo and evaporated. The residue was distilled in vacuo to give 10a. Yield 32.8 g (70 percent); colorless liquid; b.p.: 70–72 °C (3 mbar); MS (ESI):m/z = 111 ([M+H]+); 1H NMR (500 MHz, CDCl3):d = 9.84 (s, 1H), 7.36 (d, J = 1.4 Hz, 1H), 6.68 (d,J = 1.4 Hz, 1H), 3.91 (s, 3H) ppm; 13C NMR (126 MHz,CDCl3): d = 185.8, 150.9, 131.8, 105.8, 39.2 ppm.

Reference： [1] Monatshefte fur Chemie, 2016, vol. 147, # 9, p. 1629 - 1636

2
[ 25016-20-0 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: for 2 h; Heating / reflux Stage #2: With hydrogen In toluene for 8 h; Heating / reflux	A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 mL) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension OF PD-C (10 wtpercent, 9.3 g) in toluene (500 mL), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 mmHg)

Reference： [1] Patent: WO2004/58702, 2004, A2, . Location in patent: Page 31; 24

3
[ 84547-60-4 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogen In toluene for 8 h; Heating / reflux	A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 mL. The aqueous was chilled to 0 °C, acidified with concentrated HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20percent aqueous sodium hydroxide (850 ML) at 40 °C. The reaction mixture was heated at 80 °C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38percent). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wtpercent, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 MMHG).

Reference： [1] Patent: WO2004/58763, 2004, A1, . Location in patent: Page 39-40

4
[ 3920-50-1 ]
[ 74-88-4 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
51.4%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	Add 1H-pyrazole-3-carbaldehyde (4.02 g, 41.8 mmol) to a 100 mL two-necked flask.Potassium carbonate (11.5 g, 83.2 mmol) and N,N-dimethylformamide (35 mL),Methyl iodide (3.89 mL, 62.5 mmol) was then added and stirred at room temperature overnight.Add water, extract with ethyl acetate (40 mL×6),The organic phase was washed with water (80 mL) and brine (EtOAc)Filter by suction, spin dry, and the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate (v/v) = 10/1),A pale yellow oil (2.37 g, 51.4percent) was obtained.

Reference： [1] Patent: CN108690016, 2018, A, . Location in patent: Paragraph 0420; 0422; 0423

5
[ 67751-23-9 ]
[ 60-34-4 ]
[ 27258-32-8 ]
[ 27258-33-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: With sodium hydroxide In water at 0 - 20℃; Stage #2: With hydrogenchloride In water for 4 h; Stage #3: With sodium hydroxide In water	12. Preparation of 1-methylpyrazole-3-carbaldehyde from 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-oneWith cooling, methylhydrazine (151.3 g, 3.29 mol) was added dropwise to a solution of NaOH (131.4 g, 3.29 mol) in water (1700 ml). 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one (569 g, 3.28 mol) was then added dropwise at room temperature, and the mixture was stirred overnight. Hydrochloric acid (36percent strength, 219.6 g, 2.17 mol) was added, and the reaction mixture was stirred for 4 h. Using aqueous sodium hydroxide solution (10percent strength), the reaction mixture was then adjusted to a pH of 9.4. After four extractions with methylene chloride (500 ml), the organic phases were washed with water, dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. According to GC analysis, the oily residue had a purity of 73percent. In addition to the desired 1-methylpyrazole-3-carbaldehyde, the residue contained, as a byproduct, 10.7percent of the 5-carbaldehyde. This was removed by distillation under reduced pressure (transition temperature: 55° C. at 2.5 to 2.3 mbar). The yield of 1-methylpyrazole-3-carbaldehyde was 53percent. ¹H-NMR (CDCl₃): δ=4.05 (s, 3H) 6.8 (s, 1H), 7.5 (s, 1H), 9.95 ppm (s, 1H).

Reference： [1] Patent: US2010/174094, 2010, A1, . Location in patent: Page/Page column 16

6
[ 84547-62-6 ]
[ 27258-32-8 ]

Reference： [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 16, p. 2715 - 2723

[ 27258-32-8 ] Synthesis Path-Downstream 1~12

1
[ 25016-20-0 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
63%		A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 mL) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension OF PD-C (10 wtpercent, 9.3 g) in toluene (500 mL), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 mmHg)

Reference： [1]Patent: WO2004/58702,2004,A2 .Location in patent: Page 31; 24

2
[ 84547-60-4 ]
[ 27258-32-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogen;palladium 10% on activated carbon; In toluene; for 8h;Heating / reflux;	A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 mL. The aqueous was chilled to 0 °C, acidified with concentrated HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20percent aqueous sodium hydroxide (850 ML) at 40 °C. The reaction mixture was heated at 80 °C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38percent). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wtpercent, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 MMHG).

Reference： [1]Patent: WO2004/58763,2004,A1 .Location in patent: Page 39-40

3
[ 911491-26-4 ]
[ 27258-32-8 ]
N-(4-fluorobenzyl)-3-hydroxy-9,9-dimethyl-8-[(1-methyl-1H-pyrazol-3-yl)methyl]-4-oxo-6,7,8,9-tetrahydro-4H-pyrazino[1,2-a]pyrimidine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 48h;	To a solution of N-(4-fluorobenzyl)-3-hydroxy-9,9-dimethyl-4-oxo-6,7,8,9-tetrahydro- 4H-pyrazino[l,2-alpha]pyrimidine-2-carboxamide (prepared as described in Example 1, Step 1-2) in MeOH and AcOH (5 eq.) was added l-methyl-lH-pyrazole-3-carbaldehyde (2 eq.) and then NuaBEta3CNu (1.5 eq.).The mixture was left to stir for 48 hours at room temperature during which time further additions of the aldehyde (1.5 eq.) was necessary to drive the reaction to completion. After concentration under reduced pressure the crude residue was purified by RP HPLC (Ci 8, 5 muM, H2psi/MeCN with 1percent of TFA as eluant) affording the title product as TFA salt. iH-NMR (300 MHz, d6-DMSO) delta 12.32 (bs, 1 H), 9.51 (t, J= 6.3 Hz, 1 H), 7.74 (d, J = 1.5 Hz, IH), 7.38 (dd, J= 8.6 Hz, J= 5.7 Hz, 2 H), 7.18 (t, J= 8.6 Hz, 2 H), 6.36 (d, J= 1.5 Hz, 1 H), 4.49 (d, J= 6.3 Hz, 2 H), 4.14 (br. S, 2 H), 3.86 (m, 5 H), 3.37 (bs, 2 H), 1.77 (s, 6 H); MS (ES) C22H25FN6O3 requires 440, found: 441 (M+H.div.).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4245 - 4249
[2]Patent: WO2006/103399,2006,A1 .Location in patent: Page/Page column 69

4
[ 27258-32-8 ]
[ 942316-95-2 ]

Yield	Reaction Conditions	Operation in experiment
74.4%		(E)-2-terr-butoxycarbonylamino-3-(l-methyl-lH-pyrazol-3- yl)-acrylic acid methyl ester: Boc-methyl-2-(dimethylphosphono)glycinate (1.620 g, 5.45 mmol) was dissolved in CH2CI2 (10 mL) and stirred under nitrogen at it To this solution was added DBU (0.753 mL, 4.99 mmol) and the mixture was stirred for 10 min, followed by dropwise addition of a solution of 1 -methyl- lH-pyrazole-3- carbaldehyde (0.5 g, 4.54 mmol) in CH2Cl2 (10 mL) over 15-20 min. Stirring was continued at rt overnight. The solvent was removed on a rotary evaporator and the residue was taken up in a mixture OfCH2Cl2ZEtOAc, washed with 5percent citric acid and <n="159"/>brine, then dried over anhydrous sodium sulfate, filtered and evaporated. The residue was dissolved in methylene chloride and charged to a 120 g silica gel cartridge which was eluted with a 30 min gradient from 0-60percent EtOAc in hexane to provide the olefin product (0.95 g, 74.4percent) as a thick viscous oil. 1HNMR (500 MHz, CDCl3) delta: 8.49 (1 H, s), 7.32 (1 H, d, J=2.2 Hz), 6.50 (1 H, s), 6.28 (1 H, d, /=2.2 Hz), 3.94 (3 H, s), 3.84 (3 H, s), 1.48 (9 H, s). LCMS m/z 226. lv(M+H-tBu)+; 182.2 (M+H-Boc)+.

Reference： [1]Patent: WO2007/70826,2007,A1 .Location in patent: Page/Page column 156-157

5
[ 121056-95-9 ]
[ 27258-32-8 ]
[ 942316-95-2 ]

Yield	Reaction Conditions	Operation in experiment
74.4%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃;	Boc-methyl-2-(dimethylphosphono)glycinate (1.620 g, 5.45 mmol) was dissolved in Ceta2CI2 (10 mL) and stirred under nitrogen at rt. To this solution was added DBU (0.753 mL, 4.99 mmol) and the mixture was stirred for 10 min, followed by dropwise addition of a solution of 1 -methyl- IH- pyrazole-3-carbaldehyde (0.5 g, 4.54 mmol) in CH2Cl2 (10 mL) over 15-20 min. Stirring was continued at rt overnight. The solvent was removed on a rotary evaporator and the residue was taken up in a mixture of CH2Cl2ZEtOAc, washed with 5percent citric acid and brine, then dried over anhydrous sodium sulfate, filtered and evaporated. The residue was dissolved in methylene chloride and charged to a 120 g silica gel cartridge which was eluted with a 30 min gradient from 0-60percent EtOAc in hexane to provide the olefin product (0.95 g, 74.4percent) as a thick viscous oil. MS: m/z 226.1 [M + H-IBu]+. 1H NMR (500 MHz, CDCl3) delta: 8.49 (1 H, s), 7.32 (1 H, d, J=2.2Hz), 6.50 (1 H, s), 6.28 (1 H, d, J=2.2 Hz), 3.94 (3 H, s), 3.84 (3 H, s), 1.48 (9 H, s) ppm.

Reference： [1]Patent: WO2008/157162,2008,A1 .Location in patent: Page/Page column 94-95

6
[ 27258-32-8 ]
[ 1214997-78-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2715 - 2723

7
[ 84547-62-6 ]
[ 27258-32-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2715 - 2723

8
[ 264264-31-5 ]
[ 27258-32-8 ]
[ 1204828-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; for 1h;Molecular sieve;	/.7.1 Intermediate 21; A 25ml round-bottomed flask was charged with lithium chloride (0.366 g, 8.64 mmol), 1 -methyl- lH-pyrazole- 3-carbaldehyde (0.951 g, 8.64 mmol), and tert-butyl 7-acetyl-4,5-dihydro-lH-benzo[d]azepine-3(2H)- carboxylate (2.5 g, 8.64 mmol) in acetonitrile (10 ml) to give a colourless solution. DBU (1.302 ml, 8.64 mmol) was added and 4A molecular sieves. The reaction was stirred for one hour.The solvent was evaporated and the residue was taken up into ethyl acetate and washed with 5percent citric acid (x2), saturated sodium bicarbonate, and dried and evaporated. The residue was purified by Biotage 5Og SNAP column using 50percent EtOAc/ Petrol to yield pure (E)-tert-butyl 7-(3-(l-methyl-lH-pyrazol-3-yl)acryloyl)-4,5-dihydro-lH- benzo[d]azepine-3(2H)-carboxylate (6.82 mmol)MS ES+ : 3261H NMR (400 MHz, MeOD): delta 7.80 - 7.85 (m, 2H), 7.64 - 7.66 (m, 2H), 7.60 - 7.63 (m, IH), 7.27 - 7.32 (m, IH), 6.75 - 6.78 (m, IH), 3.92 (s, 3H), 3.56 (br. s., 4H), 2.95 - 3.02 (m, 4H), 1.44 (s, 9H)

Reference： [1]Patent: WO2010/7382,2010,A1 .Location in patent: Page/Page column 32-33

9
[ 27258-32-8 ]
4-bromo-1-methyl-1H-pyrazole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 50℃; for 2h;	To a solution of <strong>[27258-32-8]1-methyl-1H-pyrazole-3-carbaldehyde</strong> (150 g, 1.36 mol) in DMF (1000 mL) was added NBS (240 g, 1.35 mol). The resulting solution was stirred for 2 h at 50° C. and then was quenched by the addition of ice water (2000 mL). The reaction mixture was cooled to ?10° C. with an ice/salt bath, and the solids were collected by filtration to provide the desired product as a white solid (200 g, 78percent). 1H NMR (300 MHz, CDCl3): delta 9.90 (d, J=0.7 Hz, 1H), 7.46 (s, 1H), 3.96 (s, 3H) ppm.
61.3%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 3 - 20℃;	13.1 Preparation of 4-bromo-<strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong> by bromination of <strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong>At 3-5° C., a solution of N-bromosuccinimide (NBS, 64.6 g, 0.36 mol) in dimethyl-formamide (DMF, 160 ml) was added dropwise (slightly exothermic) to a solution of <strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong> (40 g, 0.36 mol) in DMF (320 ml). The reaction mixture was then heated to room temperature and stirred for a further 2 h. The reaction mixture was then added with stirring to a mixture of water (1400 ml) and aqueous sodium hydroxide solution (conc., 15 ml) and extracted four times with methyl tert-butyl ether (MTBE, 100 ml). The organic phases were combined and washed with saturated NaCl solution, dried over magnesium sulfate and filtered, and the solvent was then removed under reduced pressure. This gave 4-bromo-<strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong> as a solid (42.9 g, 98percent pure according to GC analysis, yield 61.3percent).1H-NMR (CDCl3): delta=4.0 (s, 3H), 7.55 (s, 1H), 9.95 ppm (s, 1H); 13C-NMR (CDCl3): delta=40.3, 95.1, 133.0, 146.5, 184.6 ppm.

Reference： [1]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0197-0198
[2]Patent: US2010/174094,2010,A1 .Location in patent: Page/Page column 16

10
[ 67751-23-9 ]
[ 60-34-4 ]
[ 27258-32-8 ]
[ 27258-33-9 ]

Yield	Reaction Conditions	Operation in experiment
53%; 10.7%Chromat.		12. Preparation of 1-methylpyrazole-3-carbaldehyde from 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-oneWith cooling, methylhydrazine (151.3 g, 3.29 mol) was added dropwise to a solution of NaOH (131.4 g, 3.29 mol) in water (1700 ml). 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one (569 g, 3.28 mol) was then added dropwise at room temperature, and the mixture was stirred overnight. Hydrochloric acid (36% strength, 219.6 g, 2.17 mol) was added, and the reaction mixture was stirred for 4 h. Using aqueous sodium hydroxide solution (10% strength), the reaction mixture was then adjusted to a pH of 9.4. After four extractions with methylene chloride (500 ml), the organic phases were washed with water, dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. According to GC analysis, the oily residue had a purity of 73%. In addition to the desired 1-methylpyrazole-3-carbaldehyde, the residue contained, as a byproduct, 10.7% of the 5-carbaldehyde. This was removed by distillation under reduced pressure (transition temperature: 55 C. at 2.5 to 2.3 mbar). The yield of 1-methylpyrazole-3-carbaldehyde was 53%. 1H-NMR (CDCl3): delta=4.05 (s, 3H) 6.8 (s, 1H), 7.5 (s, 1H), 9.95 ppm (s, 1H).

Reference： [1]Patent: US2010/174094,2010,A1 .Location in patent: Page/Page column 16

11
[ 27258-32-8 ]
[ 1089212-37-2 ]

Yield	Reaction Conditions	Operation in experiment
66.8%	With diethylamino-sulfur trifluoride; In dichloromethane; at -20 - 20℃;	17. Preparation of 3-difluoromethyl-1-methylpyrazole from <strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong>At -20° C., (diethylamino)sulfur trifluoride (DAST, 87.8 g, 0.54 mol) was added dropwise to a solution of <strong>[27258-32-8]1-methylpyrazole-3-carbaldehyde</strong> (20 g, 0.18 mol) in methylene chloride (200 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then added carefully to ice/water (400 g) and extracted twice with methylene chloride (100 ml each). The combined organic phase was washed twice with water (100 ml each) and twice with NaCl solution (100 ml each) and dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was separated by fractional distillation. 3-Difluoromethyl-1-methylpyrazole (16.5 g, transition temperature 141° C. at 570 mbar) was isolated in a purity of 95percent. This corresponds to a yield of 66.8percent.
	With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 20℃;	To a solution of <strong>[27258-32-8]1-methyl-1H-pyrazole-3-carbaldehyde</strong> (4.00 g, 36.33 mmol) in CH2Cl2 (50 mL) at 0° C. was added DAST (23.4 g, 145.17 mmol, 4.00 equiv) dropwise. The reaction mixture was stirred overnight at room temperature and then was quenched by the addition of saturated NaHCO3 (100 mL), and extracted with CH2Cl2 (3×200 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated to provide the desired product as an oil (4.8 g, crude) which was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3): delta 7.32-7.37 (m, 1H), 6.44-6.45 (t, 1H), 6.80 (m, 1H), 3.90 (s, 3H) ppm.

Reference： [1]Patent: US2010/174094,2010,A1 .Location in patent: Page/Page column 17
[2]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0170-0171

12
[ 4309-26-6 ]
[ 27258-32-8 ]
[ 1309584-49-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium acetate; acetic acid; for 10h;Reflux;	Example 4Synthetic Pathway of Compound D (7084175)(E)-3-(3-(dihydroxyamino)phenyl)-2-(2-(1-methyl-1H-pyrazol-3-yl)vinyl)quinazolin-4(3H)-oneA mixture of 2-methyl-3-(3-nitrophenyl)-3H-quinazolin-4-one (for synthesis 1 see preparation of Compound A 165 mg, 0.6 mmol), <strong>[27258-32-8]1-methyl-1H-pyrazole-3-carbaldehyde</strong> (120 mg, 0.70 mmol) and NaOAc (53 mg, 0.70 mmol) in glacial acetic acid (3.0 ml) was heated at reflux 10 hours. After the reaction mixture was allowed to cool to RT the resulting precipitate was collected by vacuum filtration, washed with water and recrystallized from EtOH to afford 114 mg (51percent) of the target compound.

Reference： [1]Patent: US2011/129463,2011,A1 .Location in patent: Page/Page column 10

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Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 27258-32-8 ]

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[ CAS No. 27258-32-8 ] {[proInfo.proName]}

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[ 27258-32-8 ] Synthesis Path-Upstream 1~6

[ 27258-32-8 ] Synthesis Path-Downstream 1~12

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Aldehydes

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Pyrazoles

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[ 27258-32-8 ]

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[ 27258-32-8 ]