[ CAS No. 5622-36-6 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 5622-36-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5622-36-6 ]

SDS Specification

Alternatived Products of [ 5622-36-6 ]

Product Details of [ 5622-36-6 ]

CAS No. :	5622-36-6	MDL No. :	MFCD04038669
Formula :	C₁₂H₁₁NO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	PCUOFKCRVNHDEB-UHFFFAOYSA-N
M.W :	201.22	Pubchem ID :	1514202
Synonyms :

Calculated chemistry of [ 5622-36-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.17
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.61
TPSA :	39.19 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	1.99
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	2.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.64
Solubility :	0.465 mg/ml ; 0.00231 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.732 mg/ml ; 0.00364 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.19
Solubility :	0.0131 mg/ml ; 0.000065 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Safety of [ 5622-36-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H302-H315	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5622-36-6 ]

* 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 [ 5622-36-6 ]
Downstream synthetic route of [ 5622-36-6 ]

[ 5622-36-6 ] Synthesis Path-Upstream 1~2

1
[ 67-56-1 ]
[ 5622-34-4 ]
[ 5622-36-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: Reflux Stage #2: With sodium hydroxide In ethyl acetateCooling with ice	Example 1. Preparation of 6-((5)-l-(6-(l-methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[3,4- δ][l,3,4]thiadiazol-3-yl)ethyl)quinoline (compound 1); [0064] As shown in step i of Scheme 1, concentrated sulfuric acid (206 mL, 3.868 mol) was added dropwise to a solution of 2-(quinolin-6-yl)acetic acid (compound 1001, 658.2 g, 3.516 mol, Okeanos Tech Co., Cat. No. OK-J-05024) in 6.5 liters of methanol. During the addition, a slight exotherm was observed. After the addition was complete, the reaction was stirred at reflux for 4 hours. After cooling, the volatiles were removed under reduced pressure, the resulting residue was diluted with 4 liters of ethyl acetate, cooled in an ice bath, treated with 2N NaOH (2.1 liters, 1.2 equiv.) until a pH of 4 was achieved, and then treated with saturated sodium bicarbonate until a pH of 8 was achieved. The layers were separated and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate, washed with water, washed with brine, dried over anhydrous MgSO₄, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acetate as a clear brown oil (compound 1002, 696.8 g, 98 percent yield): ESMS (M+l), 202.14; ¹H NMR (300.0 MHz, DMSO-d₆) δ 8.90 (IH, dd, J = 1.7, 4.2 Hz), 8.14 - 8.10 (IH, m), 8.08 (IH, d, J = 8.7 Hz), 7.72 (IH, d, J = 1.4 Hz), 7.65 (IH, dd, J = 2.0, 8.7 Hz), 7.40 (IH, dd, J = 4.2, 8.3 Hz), 3.83 (2H, s), 3.73 (3H, s).
85%	at 20℃; for 6 h;	To a solution of 2-(quinolin-6-yl)acetic acid (2.0 g, 11 mmol) in methanol (40 mL) wasadded concentrated sulphuric acid (0.2 mL). The mixture was stirred at roomtemperature for 6 hours. The reaction mass was poured into water and the resulting solution was neutralised with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2504 and evaporated in vacuo to give methyl 2-(quinolin-6-yl)acetate (1.8 g, 85percent). LCMS: m/z202.25 [M+H].
76%	With thionyl chloride In methanol at 0℃; for 2 h; Reflux	2-(quinolin-6-yl)acetic acid (12.0 g, 0.064 mol) was dissolved in dry MeOH (120 mL) and cooled to 0 °C. SOCl₂ (7.0 mL, 0.096 mol) was added, and the reaction mixture was refluxed for 2 h. The reaction mixture was concentrated under reduced pressure and the resultant residue was dissolved in EtOAc, washed with water and brine, dried over anhydrous Na₂SO/t, filtered, and concentrated under reduced pressure. The resultant residue was purified by columnchromatography (20 - 25percent EtOAc/petroleum ether) to afford the title compound (9.8 g, 76percent).TLC: 20percent MeOH/CH₂Cl₂, Rf= 0.6. ^lU NMR (300 MHz, DMSO-d₆) δ ppm 8.86 (dd, J= 4.3, 1.6 Hz, 1H), 8.32 - 8.29 (m, 1H), 7.97 (d, J= 8.6 Hz, 1H), 7.84 (m, 1H), 7.66 (dd, J= 8.8, 2.0 Hz, 1H), 7.50 (dd, J= 8.2, 4.3 Hz, 1H), 3.90 (s, 2H), 3.63 (s, 3H).

73.6%	for 3 h; Heating / reflux	To a stirred solution of quinolin-6-yl-acetic acid (10 g, 53.0 mmol) in 100 ml of methanol was added 2.5 ml of concentrated H₂SO₄ The mixture was then heated to reflux for 3 hours. The reaction mixture was concentrated to give a brown residue, which was diluted with 100 ml of dichloromethane, washed with sat. aq.NaHCO₃ and brine, then the organic layer was dried over anhydrous Na₂Sψ₄ and concentrated to return title compound as a brown oil (7.9 g, 73.6percent).
72.6%	Stage #1: at 0 - 5℃; for 2 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In water; ethyl acetate	To a suspension of compound 2 (60 g, 0.32 mol) in MeOH (600 mL) cooled to 0~5°C, SOCI₂ (30 mL, 0.35 mol) was added dropwise. After the mixture was heated to reflux for 2 h, the mixture was evaporated under reduced pressure, and the residue was taken up with EtOAc (600 mL). The mixture was washed with aq. NaHCO₃ and brine, dried over Na₂SO₄ and concentrated to give crude product, which was purified via a silica column chromatography (EtOAc: Petroleum ether = 1 :5) to give pure compound 3 (50 g, 72.6percent) as a yellow oil. ¹H NMR (400 MHz, CDCI₃): δ 8.898-8.878 (dd, 1 H), 8.130-8.055 (m, 2H), <n="31"/>7.718 (s, 1 H), 7.670-7.634 (dd, 1 H), 7.407-7.365 (q, 1 H), 4.207-4.135(q, 2 H), 3.799(s, 2H), 1.279-1.232 (t, 3H).

Reference： [1] Patent: WO2010/59668, 2010, A1, . Location in patent: Page/Page column 20-21
[2] Patent: WO2016/8011, 2016, A1, . Location in patent: Page/Page column 67
[3] Patent: WO2013/19682, 2013, A1, . Location in patent: Page/Page column 117
[4] Patent: WO2008/144767, 2008, A1, . Location in patent: Page/Page column 110; 115
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6651 - 6665
[6] Patent: WO2007/138472, 2007, A2, . Location in patent: Page/Page column 28-29

2
[ 1197-55-3 ]
[ 5622-36-6 ]

Reference： [1] Patent: WO2013/19682, 2013, A1,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6651 - 6665

[ 5622-36-6 ] Synthesis Path-Downstream 1~12

1
[ 67-56-1 ]
[ 5622-34-4 ]
[ 5622-36-6 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example 1. Preparation of 6-((5)-l-(6-(l-methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[3,4- delta][l,3,4]thiadiazol-3-yl)ethyl)quinoline (compound 1); [0064] As shown in step i of Scheme 1, concentrated sulfuric acid (206 mL, 3.868 mol) was added dropwise to a solution of 2-(quinolin-6-yl)acetic acid (compound 1001, 658.2 g, 3.516 mol, Okeanos Tech Co., Cat. No. OK-J-05024) in 6.5 liters of methanol. During the addition, a slight exotherm was observed. After the addition was complete, the reaction was stirred at reflux for 4 hours. After cooling, the volatiles were removed under reduced pressure, the resulting residue was diluted with 4 liters of ethyl acetate, cooled in an ice bath, treated with 2N NaOH (2.1 liters, 1.2 equiv.) until a pH of 4 was achieved, and then treated with saturated sodium bicarbonate until a pH of 8 was achieved. The layers were separated and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate, washed with water, washed with brine, dried over anhydrous MgSO4, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acetate as a clear brown oil (compound 1002, 696.8 g, 98 percent yield): ESMS (M+l), 202.14; 1H NMR (300.0 MHz, DMSO-d6) delta 8.90 (IH, dd, J = 1.7, 4.2 Hz), 8.14 - 8.10 (IH, m), 8.08 (IH, d, J = 8.7 Hz), 7.72 (IH, d, J = 1.4 Hz), 7.65 (IH, dd, J = 2.0, 8.7 Hz), 7.40 (IH, dd, J = 4.2, 8.3 Hz), 3.83 (2H, s), 3.73 (3H, s).
85%	With sulfuric acid; at 20℃; for 6h;	To a solution of 2-(quinolin-6-yl)acetic acid (2.0 g, 11 mmol) in methanol (40 mL) wasadded concentrated sulphuric acid (0.2 mL). The mixture was stirred at roomtemperature for 6 hours. The reaction mass was poured into water and the resulting solution was neutralised with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2504 and evaporated in vacuo to give methyl 2-(quinolin-6-yl)acetate (1.8 g, 85percent). LCMS: m/z202.25 [M+H].
76%	With thionyl chloride; In methanol; at 0℃; for 2h;Reflux;	2-(quinolin-6-yl)acetic acid (12.0 g, 0.064 mol) was dissolved in dry MeOH (120 mL) and cooled to 0 °C. SOCl2 (7.0 mL, 0.096 mol) was added, and the reaction mixture was refluxed for 2 h. The reaction mixture was concentrated under reduced pressure and the resultant residue was dissolved in EtOAc, washed with water and brine, dried over anhydrous Na2SO/t, filtered, and concentrated under reduced pressure. The resultant residue was purified by columnchromatography (20 - 25percent EtOAc/petroleum ether) to afford the title compound (9.8 g, 76percent).TLC: 20percent MeOH/CH2Cl2, Rf= 0.6. lU NMR (300 MHz, DMSO-d6) delta ppm 8.86 (dd, J= 4.3, 1.6 Hz, 1H), 8.32 - 8.29 (m, 1H), 7.97 (d, J= 8.6 Hz, 1H), 7.84 (m, 1H), 7.66 (dd, J= 8.8, 2.0 Hz, 1H), 7.50 (dd, J= 8.2, 4.3 Hz, 1H), 3.90 (s, 2H), 3.63 (s, 3H).

73.6%	With sulfuric acid; for 3h;Heating / reflux;Product distribution / selectivity;	To a stirred solution of quinolin-6-yl-acetic acid (10 g, 53.0 mmol) in 100 ml of methanol was added 2.5 ml of concentrated H2SO4 The mixture was then heated to reflux for 3 hours. The reaction mixture was concentrated to give a brown residue, which was diluted with 100 ml of dichloromethane, washed with sat. aq.NaHCO3 and brine, then the organic layer was dried over anhydrous Na2Spsi4 and concentrated to return title compound as a brown oil (7.9 g, 73.6percent).
72.6%		To a suspension of compound 2 (60 g, 0.32 mol) in MeOH (600 mL) cooled to 0~5°C, SOCI2 (30 mL, 0.35 mol) was added dropwise. After the mixture was heated to reflux for 2 h, the mixture was evaporated under reduced pressure, and the residue was taken up with EtOAc (600 mL). The mixture was washed with aq. NaHCO3 and brine, dried over Na2SO4 and concentrated to give crude product, which was purified via a silica column chromatography (EtOAc: Petroleum ether = 1 :5) to give pure compound 3 (50 g, 72.6percent) as a yellow oil. 1H NMR (400 MHz, CDCI3): delta 8.898-8.878 (dd, 1 H), 8.130-8.055 (m, 2H), <n="31"/>7.718 (s, 1 H), 7.670-7.634 (dd, 1 H), 7.407-7.365 (q, 1 H), 4.207-4.135(q, 2 H), 3.799(s, 2H), 1.279-1.232 (t, 3H).

Reference： [1]Patent: WO2010/59668,2010,A1 .Location in patent: Page/Page column 20-21
[2]Patent: WO2016/8011,2016,A1 .Location in patent: Page/Page column 67
[3]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 117
[4]Patent: WO2008/144767,2008,A1 .Location in patent: Page/Page column 110; 115
[5]Journal of Medicinal Chemistry,2013,vol. 56,p. 6651 - 6665
[6]Patent: WO2007/138472,2007,A2 .Location in patent: Page/Page column 28-29

2
[ 5622-36-6 ]
2-(6-quinolinyl)ethanamidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride;trimethylaluminum; In toluene;	EXAMPLE 8A 2-(6-Quinolinyl)ethanamidine hydrochloride 21.4 g (400 mmol) of ammonium chloride are suspended in 400 ml of dry toluene and the suspension is cooled to 0° C. 200 ml of a 2M solution of trimethylaluminium in toluene are added dropwise and the mixture is stirred at room temperature until the evolution of gas is complete. After addition of 17.9 g (88.9 mmol) of <strong>[5622-36-6]methyl 6-quinolinylacetate</strong>, the reaction mixture is stirred overnight at 100° C. (bath). The cooled reaction mixture is treated with 90 g of silica gel and then stirred at room temperature for a further 15 min. The solid is then filtered off with suction, and the filter cake is washed several times more with dichloromethane/methanol 10/1. The filtrate is concentrated. 1H-NMR (DMSO-d6): delta/ppm 3.97 (s, 2 H), 7.54-9.31 (m, 6 H).

Reference： [1]Patent: US2002/198377,2002,A1

3
[ 5622-36-6 ]
[ 943541-37-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With selenium(IV) oxide; In 1,4-dioxane; for 72h;Heating / reflux;	To the solution of <strong>[5622-36-6]methyl 6-quinolineacetate</strong> (1.2 g, 6 mmmol) in dioxane (30 mL) was added Selenium dioxide (1.65 g, 15 mmol). The mixture was heated to reflux for 3 days, cooled to room temperature, filtered through Celite and concentrated. The residue was purified by chromatography (methylene chloride to 5percent ethyl acetate in chloride) to a white solid (0.75 g, 58percent). 1H-NMR (CDCl3): delta 9.07-9.06 (IH, q, J = 1.7, 2.5 Hz), 8.62-8.61 (IH, d, / = 1.7 Hz), 8.32-8.31 (2H, m), 8.22-8.20 (IH, d, J = 8.8 Hz), 7.54-7.51 (IH, q, J = 8.8Hz), 4.05 (3H, s).

Reference： [1]Patent: WO2007/75567,2007,A1 .Location in patent: Page/Page column 114

4
[ 5622-36-6 ]
[ 943541-42-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 3-chloro-benzenecarboperoxoic acid; In 1,2-dimethoxyethane; at 20℃; for 2h;	m-Perchlorobenzoic acid (6.85g, 39.8piiotamol) was added to a solution of commercially available <strong>[5622-36-6]quinolin-6-yl-acetic acid methyl ester</strong> (5.00g, 24.8mmol) in 1,2- dimethoxyethane at room temperature and stirred for 2 hours. Water was added and . the solution was basified to pH 9-10 with saturated potassium carbonate and the product was extracted with ethyl acetate to give quantitative yield of (1-hydroxy- quinolin-6-yl)-acetic acid methyl ester. 1H NMR (400 MHz, CDCl3) S 7.99 (d, IH, J=8.4Hz), 7.93 (d, IH, J=8.4Hz), 7.65 (m, IH), 7.60 (m, IH), 732 (d, IH, J=8.8Hz), 7.19 (s, IH), 3.74 (s, 2H), 3.65 (s, 3H).
800 mg		771-CPBA (0.77 g, 4.4 mmol) was added to a solution of <strong>[5622-36-6]methyl 2-(quinolin-6-yl)acetate</strong>(0.6 g, 2.98 mmol) in DME (5 mL) at rt and stirred for 2 h. The reaction mixture was diluted with water and basified to pH -10 using saturated aq. K2C03. The reaction mixture was extracted with EtOAc, dried over anhydrous Na2SO/t, filtered, and concentrated under reduced pressure to afford the title compound (800 mg). TLC: 10percent MeOH/CHCl3, Rf= 0.1. lU NMR (300 MHz, DMSO- d6) delta ppm 8.55 - 8.53 (m, 1H), 8.48 - 8.45 (m, 1H), 7.95 (m, 1H), 7.86 (m, 1H), 7.72 - 7.69 (m, 1H), 7.45 - 7.41 (m, 1H), 3.92 (s, 2H), 3.63 (s, 3H).

Reference： [1]Patent: WO2007/75567,2007,A1 .Location in patent: Page/Page column 122-123
[2]Journal of the American Chemical Society,2017,vol. 139,p. 16822 - 16829
[3]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 117

5
[ 5622-36-6 ]
[ 227809-77-0 ]

Yield	Reaction Conditions	Operation in experiment
84%		Example 124; 6-Phenyl-2-(2-(quinolin-6-yl)ethyl)pyridaziii-3(2//)-oiie.(1) To a 25 mL round-bottomed flask was added lithium aluminum hydride (0.057 g, 1.5 mmol, Strem Chemicals) and THF (8.0 mL). The mixture was cooled to - 30 °C and <strong>[5622-36-6]methyl 2-(quinolin-6-yl)acetate</strong> (0.30 g, 1.5 mmol, Tyger) in 2 mL THF was added over 1 minute. The mixture was stirred at -30 °C for 30 min, then quenched with 0.056 mL H2O. The solution was allowed to warm to rt and 0.056 mL 15percent aq. NaOH and then 0.168 mL H2O were added. The mixture was stirred for 15 minutes and then filtered. The filtercake was washed with THF and the filtrate was concentrated. Purification by silica gel chromatography (0.5 to 5.0percent MeOH (2 M in NH3)/CH2C12) afforded the title compound as a yellow solid (0.22 g, 84percent yield). MS (ESI pos. ion) m/z (MH+): 174. Calc'd exact mass for CHHI 1NO: 173. 1H NMR (400 MHz, DMSO-^6) delta ppm 8.83 (dd, J= 4.2, 1.7 Hz, 1 H), 8.28 (dd, J = 8.3, 0.9 Hz, 1 H), 7.93 (d, J= 8.6 Hz, 1 H), 7.77 (d, J= 1.2 Hz, 1 H), 7.65 (dd, J= 8.6, 2.0 Hz, 1 H), 7.49 (dd, J= 8.3, 4.2 Hz, 1 H), 4.73 (X, J = 5.2 Hz, 1 H), 3.72 (dt, J= 6.8, 5.3 Hz, 2 H), 2.92 (t, J= 6.8 Hz, 2 H).
84%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4.16667h;	To a mixture of LiAIH4 (680 mg, 17.9 mmol) in THE (50 mL) at 0 °C was added <strong>[5622-36-6]methyl 2-(quinolin-6-yl)acetate</strong> (1.8 g, 8.9 mmol). The mixture was stirred for 10 minutes at this temperature, after which the reaction mass was slowly warmed to room temperatureand stirred for 4 hours. After complete consumption of the starting material as determined by TLC, the reaction mixture was quenched with ethyl acetate (3 mL) and saturated ammonium chloride solution (20 mL) at 0 °C, filtered and concentrated to give 2-(quinolin-6-yl)ethan-1 -ol (1.3 g, 84percent). LCMS: m/z 174.28 [M+H].

Reference： [1]Patent: WO2008/103277,2008,A2 .Location in patent: Page/Page column 167
[2]Patent: WO2016/8011,2016,A1 .Location in patent: Page/Page column 67

6
[ 5622-36-6 ]
[ 5622-41-3 ]

Yield	Reaction Conditions	Operation in experiment
93.9%	With hydrazine; In ethanol; for 1.5h;Heating / reflux;	Quinolin-6-yl-acetic acid methyl ester (15g, 74.5mmol) was dissolved in 90 ml of ethanol, and hydrazine hydrate (16.6mL, 342.9mmol) was added dropwise to the solution while stirring. The resulting solution was heated to reflux for 1.5 h. Excess ethanol and hydrazine hydrate were distilled off and the contents <n="112"/>allowed to cool. The precipitate was collected via filtration, washed with cold ethanol and dried in vacuo to return the title compound (15.4g, 93.9percent) as a white solid

Reference： [1]Patent: WO2008/144767,2008,A1 .Location in patent: Page/Page column 110-111

7
[ 5622-36-6 ]
[ 1022091-89-9 ]

Yield	Reaction Conditions	Operation in experiment
45.3%		To a stirred solution of <strong>[5622-36-6]quinolin-6-yl-acetic acid methyl ester</strong> (21.6 g, 107 mmol) in 150 ml of carbon tetrachloride was treated with bromine (34.4 g, 215 mmol) and heated to reflux for 4 hours. The reaction mixture was treated with 17.0 g of pyridine, and further stirred for 2 hours under reflux. After cooling down to ambient temperature, the mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate, the organic layer was washed with water and brine, dried over magnesium sulfate then evaporated under reduced pressure to give a brown residue. The residue was purified by column chromatography, eluting with petroleum (60~90°C) and then a 30:1 mixed solvent of petroleum and ethyl acetate to return title compound (13.6 g, 45.3percent) as a white crystalline solid. (300MHz, DMSO-d6): 8.89 (d, IH), 8.27 (d, IH), 8.06 (d, IH), 7.67~7.64(m, 2H), 3.82(s, 2H), 3.72(s, 3H). ES-MS m/z: 280 (M+H+).

Reference： [1]Patent: WO2008/144767,2008,A1 .Location in patent: Page/Page column 115

8
[ 50-00-0 ]
[ 5622-36-6 ]
[ 1227467-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; Hexadecyltrimethylammonium hydrogen sulfate; In toluene;Reflux;	[0065] As shown in step ii of Scheme 1, <strong>[5622-36-6]methyl 2-(quinolin-6-yl)acetate</strong> (82 g, 407.5 mmol) , paraformaldehyde (25.89 g, 862.1 mmol) , K2CO3 (101.4 g, 733.5 mmol), and hexadecyl(trimethyl)ammonium hydrogen sulfate (15.55 g, 40.75 mmol) were taken up in toluene (1.6 liters) and refluxed for 2 hours until the starting material was completely consumed, as monitored by HPLC. The reaction mixture was cooled down using an ice-water bath and filtered through diatomaceous earth. The filtrate was washed with 1 liter of water and the organic layer dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acrylate as a clear colorless oil (75.0 g). This material was used immediately without further purification in the next reaction.

Reference： [1]Patent: WO2010/59668,2010,A1 .Location in patent: Page/Page column 20-21

9
[ 5622-36-6 ]
[ 106-93-4 ]
[ 1266238-14-5 ]

Yield	Reaction Conditions	Operation in experiment
20%		Example 50 (.pound.)-1-Methyl-2-(1-(3-(1-(quinolin-6-yl)cyclopropyl)-[1 ,2,4]triazolo[4,3-b]pyridazin-6- yl)ethylidene)hydrazinecarboxamide1-Quinolin-6-yl-cyclopropanecarboxylic acid methyl ester (50.1) A solution of LDA (1.8 M solution in toluene, 14.8 ml, 26.6 mmol) was added dropwise to a solution of <strong>[5622-36-6]quinolin-6-yl-acetic acid methyl ester</strong> (2.14 g, 10.64 mmol) in dry THF (40 ml.) under a nitrogen atmosphere at -78 0C. After 30 min, 1 ,2-dibromoethane (2.40 g, 12.76 mmol) was added dropwise over 3 min. The resulting mixture was stirred for 1 h at room temperature, then quenched with satd aq. NH4CI. The mixture was extracted with DCM, washed with brine, dried over Na2SO4, and stripped of solvent. The residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient to afford 463 mg (20percent) of the title compound as yellow solid. 1H-NMR (400MHz, CDCI3) delta ppm 8.91 (dd, 1 H), 8.12 (d, 1 H), 8.07 (d, 1 H), 7.77-7.74 (m, 2H), 7.40 (dd, 1 H), 3.65 (s, 3H), 1.73-1.71 (m, 2H), 1.33-1.30 (m, 2H). LCMS (method A): [MH]+ = 228, tR = 4.37 min.
20%		LDA (1.8 M solution in toluene, 14.8 mL, 26.6 mmol) was added dropwise to a solution of <strong>[5622-36-6]quinolin-6-yl-acetic acid methyl ester</strong> (2.14 g, 10.64 mmol) in dry THF (40 mL) under nitrogen at -78 0C. After 30 min, 1 ,2-dibromoethane (2.40 g, 12.76 mmol) was added dropwise over 3 min. The resulting mixture was stirred for 1 h at rt, then quenched with saturated aqueous NH4CI, extracted with DCM, washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient to afford the title compound as a yellow solid (463 mg, 20percent). 1H- NMR (400 MHz, CDCI3) delta ppm 8.91 (dd, 1 H), 8.12 (d, 1 H), 8.07 (d, 1 H), 7.77-7.74 (m, 2H), 7.40 (dd, 1 H), 3.65 (s, 3H), 1.73-1 .71 (m, 2H), 1.33-1 .30 (m, 2H). LCMS (method A): [MH]+ = 228, tR = 4.37 min.

Reference： [1]Patent: WO2011/18454,2011,A1 .Location in patent: Page/Page column 100-101
[2]Patent: WO2011/20861,2011,A1 .Location in patent: Page/Page column 122

10
[ 5622-36-6 ]
[ 1266238-15-6 ]

Reference： [1]Patent: WO2011/18454,2011,A1
[2]Patent: WO2011/20861,2011,A1

11
[ 5622-36-6 ]
[ 1266238-16-7 ]

Reference： [1]Patent: WO2011/18454,2011,A1
[2]Patent: WO2011/20861,2011,A1

12
[ 5622-36-6 ]
C₂₁H₁₉N₅O [ No CAS ]

Reference： [1]Patent: WO2011/18454,2011,A1
[2]Patent: WO2011/20861,2011,A1

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Technical Information

? Acyl Group Substitution ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents

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[ 5622-36-6 ]

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[ CAS No. 5622-36-6 ] {[proInfo.proName]}

Quality Control of [ 5622-36-6 ]

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Calculated chemistry of [ 5622-36-6 ] Expand+

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Application In Synthesis of [ 5622-36-6 ]

[ 5622-36-6 ] Synthesis Path-Upstream 1~2

[ 5622-36-6 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 5622-36-6 ]

Esters

Related Parent Nucleus of [ 5622-36-6 ]

Quinolines

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[ 5622-36-6 ]

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[ 5622-36-6 ]