[ CAS No. 16034-46-1 ] {[proInfo.proName]}

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2D 3D

Structure of 16034-46-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 16034-46-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16034-46-1 ]

SDS Specification

Alternatived Products of [ 16034-46-1 ]

Product Details of [ 16034-46-1 ]

CAS No. :	16034-46-1	MDL No. :	MFCD00464253
Formula :	C₅H₆N₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JREJQAWGQCMSIY-UHFFFAOYSA-N
M.W :	126.11	Pubchem ID :	643158
Synonyms :		Chemical Name :	1-Methyl-1H-pyrazole-5-carboxylic acid

Calculated chemistry of [ 16034-46-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.45
TPSA :	55.12 ?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) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.83
Log Po/w (XLOGP3) :	0.09
Log Po/w (WLOGP) :	0.12
Log Po/w (MLOGP) :	-0.4
Log Po/w (SILICOS-IT) :	-0.26
Consensus Log Po/w :	0.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.02
Solubility :	11.9 mg/ml ; 0.0947 mol/l
Class :	Very soluble
Log S (Ali) :	-0.8
Solubility :	19.9 mg/ml ; 0.158 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.13
Solubility :	93.7 mg/ml ; 0.743 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 16034-46-1 ]

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

Application In Synthesis of [ 16034-46-1 ]

* 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 [ 16034-46-1 ]
Downstream synthetic route of [ 16034-46-1 ]

[ 16034-46-1 ] Synthesis Path-Upstream 1~1

1
[ 16034-46-1 ]
[ 84547-61-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere	To a solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) in tetrahydrofuran (50 mL) was added L1AIH₄ (720 mg, 18.97 mmol) in portions at 0 °C under an inert atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature then quenched by the addition of water (2 mL). The mixture was dried over by anhydrous sodium sulfate and the solids were filtered out. The filtrates were concentrated under reduced pressure to afford (1 -methyl- lH-pyrazol- 5-yl)methanol as colorless oil (1.2 g, 67 ). (ES, m/z) [M+H]⁺ 113.0 *H NMR (300 MHz, CDC1₃) δ 7.36 (d, 7 = 1.8 Hz, 1H), 6.18 (d, 7 = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H)

Reference： [1] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175
[2] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2297 - 2303[3] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2598 - 2605
[4] Patent: WO2014/151142, 2014, A1,
[5] Patent: WO2016/29454, 2016, A1, . Location in patent: Page/Page column 64

[ 16034-46-1 ] Synthesis Path-Downstream 1~8

1
[ 694-31-5 ]
[ 16034-46-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 976 - 980
    Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1073 - 1078
[2]Journal of general chemistry of the USSR,1982,vol. 52,p. 2291 - 2296
    Zhurnal Obshchei Khimii,1982,vol. 52,p. 2592 - 2598
[3]Journal of the Chemical Society,1903,vol. 83,p. 469
[4]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 778 - 784
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1071 - 1077

2
[ 16034-46-1 ]
[ 84547-84-2 ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2291 - 2296
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2592 - 2598

3
[ 67-56-1 ]
[ 16034-46-1 ]
[ 17827-60-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With thionyl chloride; at 0 - 20℃; for 12.0h;Inert atmosphere;	To a stirred solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (5 g, 39.7 mmol) in methanol (100 mL) was added thionyl chloride (103.2 mmol) under argon atmosphere at 0 C. The reaction mixture was stirred to room temperature over 12 h. The reaction mixture was cone, in vacuo, then diluted with water (100 mL), carefully quenched with sat'd aqueous NaHCC"3, and extracted with ethyl acetate (100 mL x 3). The combined organic phase was dried with anhydrous sodium sulphate, filtered and the filtrate was concentrated to give afford the title compound as a white solid which was used without further purification (5 g, 90 %) m/z 240.

Reference： [1]Patent: WO2014/151142,2014,A1 .Location in patent: Paragraph 0092
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 778 - 784
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1071 - 1077
[3]Journal of Medicinal Chemistry,2021,vol. 64,p. 941 - 957

4
[ 16034-46-1 ]
[ 18107-18-1 ]
[ 17827-60-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	In methanol; toluene; for 1.0h;	Example 92: 2-Methyl-2H-pyrazole-3-carboxylic acid methyl ester; o MeO J2-Methyl-2H-pyrazole-3-carboxylic acid (3.0 g, 24 mmol, 1.0 equiv) was dissolved in methanol (100 mL) and toluene (100 mL). The clear solution was slowly treated with (trimethylsilyl)diazomethane (24 mL of 2.0M in ether, 48 mmol, 2.0 equiv), stirred for 1 hour, concentrated in vacuo, and gave a clear oil (3.1 g, 94% yield): 1H NMR (400 MHz, DMSO- d6) δ 7.52 (d, J = 2.0Hz, 1 H), 6.86 (d, J = 2.0Hz, 1 H), 4.07 (s, 3H), 3.82 (s, 3H).

Reference： [1]Patent: WO2006/43145,2006,A1 .Location in patent: Page/Page column 120

5
[ 16034-46-1 ]
[ 137890-05-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1422 - 1424
[2]Patent: WO2018/160878,2018,A1

6
[ 16034-46-1 ]
[ 475106-18-4 ]
tert-butyl 3-((((1-methyl-1H-pyrazol-5-yl)carbonyl)amino)methyl)morpholine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
756 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 45.0h;	A mixture of 1-methyl-1H-pyrazole-5-carboxylic acid (277 mg), <strong>[475106-18-4]tert-butyl 3-(aminomethyl)morpholine-4-carboxylate</strong> (433 mg), HATU (913 mg), DIEA (0.699 ml) and DMF (8 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (756 mg). 1H NMR (300 MHz, CDCl3) δ 1.38 (9H, s), 3.13-3.54 (3H, m), 3.64 (1H, dd, J = 11.9, 2.8 Hz), 3.73 (1H, brs), 3.81-3.96 (2H, m), 3.99-4.40 (5H, m), 6.50 (1H, d, J = 2.3 Hz), 6.55-6.88 (1H, m), 7.41 (1H, d, J = 2.3 Hz).

Reference： [1]Patent: EP3342772,2018,A1 .Location in patent: Paragraph 0244

7
[ 16034-46-1 ]
[ 7499-66-3 ]
N-(6-bromo-2-naphthyl)-2-methyl-pyrazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.7%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 25℃; for 19h;Inert atmosphere;	To a mixture of 6-bromonaphthalen-2-amine (100 mg, 450.29 mumol, 1 eq), 2-methylpyrazole-3-carboxylic acid (56.79 mg, 450.29 mumol, 1 eq), HATU (222.58 mg, 585.37 mumol, 1.3 eq) in DCM (10 mL) was added Et3N (136.69 mg, 1.35 mmol, 188.02 muL, 3 eq). The mixture was stirred at 25° C. under N2 atmosphere for 19 h. The mixture was concentrated and saturated NaHCO3 (10 mL) was added, extracted with EtOAc (10 mL*3). The combined organic layers were dried over Na2SO4, filtered and concentrated to yield the residue which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 10/3, TLC: PE/EtOAc=3/1, Rf=0.45) to yield N-(6-bromo-2-naphthyl)-2-methyl-pyrazole-3-carboxamide (120 mg, 363.44 mumol, 80.7percent yield, 100.0percent purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.29 (d, J=1.8 Hz, 1H), 7.98 (s, 1H), 7.84-7.75 (m, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.61-7.49 (m, 3H), 6.71 (d, J 2.2 Hz, 1H), 4.26 (s, 3H); ES-LCMS m/z 332.0, 334.0 [M+H]+.

Reference： [1]Patent: US2019/55218,2019,A1 .Location in patent: Paragraph 0474; 0475; 0476; 0477

8
[ 16034-46-1 ]
[ 7499-66-3 ]
2-methyl-N-[6-(o-tolyl)-2-naphthyl]pyrazole-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

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Technical Information

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[ 16034-46-1 ]

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[ CAS No. 16034-46-1 ] {[proInfo.proName]}

Quality Control of [ 16034-46-1 ]

Related Doc. of [ 16034-46-1 ]

Product Details of [ 16034-46-1 ]

Calculated chemistry of [ 16034-46-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 16034-46-1 ]

Application In Synthesis of [ 16034-46-1 ]

[ 16034-46-1 ] Synthesis Path-Upstream 1~1

[ 16034-46-1 ] Synthesis Path-Downstream 1~8

Technical Information

Related Functional Groups of [ 16034-46-1 ]

Carboxylic Acids

Related Parent Nucleus of [ 16034-46-1 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 16034-46-1 ]

Related Parent Nucleus of
[ 16034-46-1 ]