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Quality Control of [ 24306-33-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 24306-33-0 ]

CAS No. :	24306-33-0	MDL No. :	MFCD00466075
Formula :	C₁₁H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	187.19	Pubchem ID :	-
Synonyms :

Safety of [ 24306-33-0 ]

Signal Word:	Class:	N/A
Precautionary Statements:	UN#:	N/A
Hazard Statements:	Packing Group:	N/A

Application In Synthesis of [ 24306-33-0 ]

* 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 [ 24306-33-0 ]
Downstream synthetic route of [ 24306-33-0 ]

[ 24306-33-0 ] Synthesis Path-Upstream 1~1

1
[ 24306-33-0 ]
[ 13669-57-3 ]

Reference： [1] Patent: WO2012/107500, 2012, A1,
[2] Patent: WO2013/38362, 2013, A1,
[3] Patent: US2013/245002, 2013, A1,
[4] Patent: US2013/324526, 2013, A1,

[ 24306-33-0 ] Synthesis Path-Downstream 1~3

1
[ 580-16-5 ]
[ 75-36-5 ]
[ 24306-33-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In dichloromethane at 0 - 20℃;	a l,2,3,4-tetrahydroquinolin-6-yl acetate. Intermediate BI Step a: To a solution of quinolin-6-ol (1.00 g, 6.88 mmol) and TEA (2.84 mL, 20.6 mmol) in DCM (50.0 mL) was added acetyl chloride (1.07 g, 13.7 mmol) dropwise at 0 °C. The reaction mixture was stirred at 20 °C for 1 hour. The reaction mixture was poured into H20 (100.0 mL) and extracted with DCM (50.0 mL x 2). The combined organic layers were washed with brine (50.0 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give an orange residue. The residue was purified by flash silica gel chromatography (20 g column, ethyl acetate in petroleum ether from 0% to 30%) to give the product of quinolin-6-yl acetate (1.20 g, 94% yield) as a yellow oil. LCMS m/z [M+H]+ = 188.0.
93%	With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	quinolin-6-yl acetate Quinolin-6-ol (10.0 g, 68.9 mmol) was solubilised in dichloromethane (100 ml) and pyridine (6.7 ml, 83 mmol) was added. Under argon, the mixture was cooled to 0°C and acetyl chloride (5.9 ml, 83 mmol; CAS-RN: [75-36-5]) was added. The mixture was stirred overnight at rt. Sat. NaHC03 solution was added and the mixture was extracted with DCM. The organic layer was washed with sat. NaCI solution, dried with Na2S04 and evaporated. The residue was purified by flash chromatography to give 12.1 g (93 % yield) of the title compound.LC-MS (Method 3): Rt= 0.64 min; MS (ESIpos): m/z = 188 [M+H]+-NMR (400 MHz, DMSO-d6) d [ppm]: 2.345 (16.00), 2.518 (0.42), 3.360 (0.49), 7.550 (1.11),7.557 (1.24), 7.560 (1.27), 7.563 (1.35), 7.570 (1.13), 7.580 (1.75), 7.586 (1.34), 7.755 (1.79),7.762 (1.61), 8.048 (1.43), 8.071 (1.32), 8.359 (0.77), 8.362 (0.77), 8.380 (0.73), 8.383 (0.74),8.900 (1.16), 8.904 (1.15), 8.910 (1.16), 8.914 (1.09)
93%	With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	quinolin-6-yl acetate Quinolin-6-ol (10.0 g, 68.9 mmol) was solubilised in dichloromethane (100 ml) and pyridine (6.7 ml, 83 mmol) was added. Under argon, the mixture was cooled to 0°C and acetyl chloride (5.9 ml, 83 mmol; CAS-RN: [75-36-5]) was added. The mixture was stirred overnight at rt. Sat. NaHC03 solution was added and the mixture was extracted with DCM. The organic layer was washed with sat. NaCI solution, dried with Na2S04 and evaporated. The residue was purified by flash chromatography to give 12.1 g (93 % yield) of the title compound.LC-MS (Method 3): Rt= 0.64 min; MS (ESIpos): m/z = 188 [M+H]+-NMR (400 MHz, DMSO-d6) d [ppm]: 2.345 (16.00), 2.518 (0.42), 3.360 (0.49), 7.550 (1.11),7.557 (1.24), 7.560 (1.27), 7.563 (1.35), 7.570 (1.13), 7.580 (1.75), 7.586 (1.34), 7.755 (1.79),7.762 (1.61), 8.048 (1.43), 8.071 (1.32), 8.359 (0.77), 8.362 (0.77), 8.380 (0.73), 8.383 (0.74),8.900 (1.16), 8.904 (1.15), 8.910 (1.16), 8.914 (1.09)

86%	With pyridine In dichloromethane at 0 - 25℃; for 8h; Inert atmosphere;	194 Example 194: Synthesis of quinolin-6-yl acetate (196 To a solution of 194 (24.0 g, 165 mmol) and pyridine (15.7 g, 198 mmol) in DCM (300 mL) was added 195 (15.5 g, 198 mmol) dropwise at 0° C. Then the mixture was stirred at 25° C. for 8 h under N2. The mixture was basified by sat. NaHCO3 solution to pH 8 and extracted by EA (2×300 mL). The organic layer was concentrated in vacuum and purified by silica gel column (0 to 36% of EA in PE) to obtain 196 (26.8 g, 86% yield, 99% purity) as yellow solid. [M+H]+ calcd for C11H9NO2 188.06, found 188.0.
86%	With pyridine In dichloromethane at 0 - 25℃; for 8h; Inert atmosphere;	49.A Step A: Preparation of quinolin-6-yl acetate (49-2). To a solution of 49-1 (24.0 g, 165 mmol) and pyridine (15.7 g, 198 mmol) in DCM (300 mL) was added acetyl chloride (15.5 g, 198 mmol) dropwise at 0 °C. Then the mixture was stirred at 25 °C for 8 h under N2. The mixture was basified by sat. NaHCO3 solution to pH=8 and extracted by EA (300 mL*2). The organic layer was concentrated in vacuum and purified by silica gel column (0 to 36% of EA in PE) to obtain 49-2 (26.8 g, 86% yield, 99% purity) as yellow solid. [M+H]+ calcd for C11H9NO2 188.06, found 188.0.
86%	With pyridine In dichloromethane at 0 - 20℃; for 8h;
69%	With pyridine at 0 - 20℃; for 3h;	1.17.1 Intermediate 17: Trifluoro-methanesulfonic acid 3-(l-methyl-l//-pyrazol-4-yl)- quinolin-6-yl ester; Step 1: Acetic acid quinolin-6-yl ester; [0330] Quinolin-6-ol (135 g, 0.93 mol) was dissolved in pyridine (500 mL) and cooled to O0C in an ice-bath under a flow of nitrogen. Acetyl chloride (79 mL, 1.1 6mol) was added to the reaction mixture slowly. Then it was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate (400 mL) and saturated aqueous NaHCO3 (200 mL). The organic phase was separated and washed with brine (5*200mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 12O g of acetic acid quinolin-6-yl ester as white solid (69 % yield).
69%	With pyridine at 0 - 20℃; for 3h;	1 Quinolin-6-ol (135 g, 0.93 mol) was dissolved in pyridine (500 mL) and cooled to O0C in an ice-bath under a flow of nitrogen. Acetyl chloride (79 mL, 1.1 6mol) was added to the reaction mixture slowly. Then it was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate (400 mL) and saturated aqueous NaHCO3 (200 mL). The organic phase was separated and washed with brine (5 x 20OmL). The organic phase was dried over Na2SOzJ, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 120 g of acetic acid quinolin-6-yl ester as white solid (69 % yield).
68.9%	With pyridine In dichloromethane at 0 - 20℃; for 8h;	To a solution of quinolin-6-ol (4.5 g, 31.0 mmol) and pyridine (3.01 ml, 37.2 mmol) in DCM (50 ml) was added acetyl chloride (2.65 ml, 37.2 mmol) at 0°C. The mixture was then stirred at rt for 8 h. The reaction was quenched with saturated NaHC03 and the mixture was extracted with DCM (30 ml) three times. The combined organic phase was washed with brine and dried over anhydrous MgS04, filtered and concentrated to give the title compound J.i (5.0 g, 68.9% yield), which was used directly in next step. LCMS (method B): [MH]+ = 188, tR = 1.64 min.
68.9%	With pyridine In dichloromethane at 0 - 20℃; for 8h;	Quinolin-6-yl acetate (A.i) To a solution of quinolin-6-ol (4.5 g, 31.0 mmol) and pyridine (3.01 ml, 37.2 mmol) in DCM (50 ml) was added acetyl chloride (2.65 ml, 37.2 mmol) at 0°C. The mixture was then stirred at rt for 8 h. The reaction was quenched with saturated NaHC03 and the mixture was extracted with DCM (30 ml) three times. The combined organic phase was washed with brine and dried over anhydrous MgS04, filtered and concentrated to give the title compound (5.0 g, 68.9% yield), which was used directly in next step. LCMS (method B): [M+H]+ = 188, tR = 1.64 min.
68.9%	With pyridine In dichloromethane at 0 - 20℃; for 8h;	Quinolin-6-yl acetate (A.i) To a solution of quinolin-6-ol (4.5 g, 31.0 mmol) and pyridine (3.01 ml, 37.2 mmol) in DCM (50 ml) was added acetyl chloride (2.65 ml, 37.2 mmol) at 0° C. The mixture was then stirred at rt for 8 h. The reaction was quenched with saturated NaHCO3 and the mixture was extracted with DCM (30 ml) three times. The combined organic phase was washed with brine and dried over anhydrous MgSO4, filtered and concentrated to give the title compound (5.0 g, 68.9% yield), which was used directly in next step. LCMS (method B): [M+H]+=188, tR=1.64 min.
68.9%	With pyridine In dichloromethane at 0 - 20℃; for 8h;	Quinolin-6-yl acetate (J.i) To a solution of quinolin-6-ol (4.5 g, 31.0 mmol) and pyridine (3.01 ml, 37.2 mmol) in DCM (50 ml) was added acetyl chloride (2.65 ml, 37.2 mmol) at 0° C. The mixture was then stirred at rt for 8 h. The reaction was quenched with saturated NaHCO3 and the mixture was extracted with DCM (30 ml) three times. The combined organic phase was washed with brine and dried over anhydrous MgSO4, filtered and concentrated to give the title compound J.i (5.0 g, 68.9% yield), which was used directly in next step. LCMS (method B): [MH]+=188, tR=1.64 min.
52%	With pyridine In dichloromethane at 0 - 20℃;	188.1 Preparation of quinoline-6-acetate To 100ml round bottom three-necked flask was added dry dichloromethane 50ml, 4.5 g (31 mmol) of 6-hydroxyquinoline and 2.9 g (37 mmol) of pyridine were sequentially added with stirring, and the mixture was cooled to 0 ° C, Acetyl chloride 2.9g (37mmol) was slowly added dropwise. When the addition was completed, the mixture was stirred at room temperature and allowed to react overnight. After treatment, the reaction solution was poured into 200ml of cold saturated aqueous sodium carbonate, the organic phase was separated, The aqueous phase was extracted with methylene chloride 50ml * 2, the combined organic phase was washed with saturated saline, dried to give the product 3g, Yield 52%, a step directly.
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃;

Reference： [1]Current Patent Assignee: D.E. SHAW RESEARCH LLC; RELAY THERAPEUTICS INC - WO2019/183367, 2019, A1 Location in patent: Paragraph 0229
[2]Current Patent Assignee: Helmholtz Association; BAYER AG - WO2021/249913, 2021, A1 Location in patent: Page/Page column 100
[3]Current Patent Assignee: Helmholtz Association; BAYER AG - WO2021/249913, 2021, A1 Location in patent: Page/Page column 100
[4]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2020/188370, 2020, A1 Location in patent: Paragraph 0917; 0918
[5]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - WO2021/102468, 2021, A1 Location in patent: Paragraph 410; 411
[6]Verma, Vishal A.; Wang, Lan; Labadie, Sharada S.; Liang, Jun; Sellers, Benjamin D.; Wang, Jian; Dong, Liting; Wang, Qiuyue; Zhang, Shuang; Xu, Zhongya; Zhang, Yexia; Niu, Yanan; Wang, Xinxin; Wai, John; Koehler, Michael F. T.; Hu, Huiyong; Alexander, Mary Kate; Nishiyama, Mireille; Miu, Anh; Xu, Yiming; Pang, Jodie; Katakam, Anand K.; Reichelt, Michael; Austin, Cary D.; Ho, Hoangdung; Payandeh, Jian; Koth, Christopher M. [Journal of Medicinal Chemistry, 2022, vol. 65, # 5, p. 4085 - 4120]
[7]Current Patent Assignee: ELI LILLY & CO - WO2008/51808, 2008, A2 Location in patent: Page/Page column 90
[8]Current Patent Assignee: ELI LILLY & CO - WO2008/144767, 2008, A1 Location in patent: Page/Page column 119
[9]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2012/107500, 2012, A1 Location in patent: Page/Page column 63
[10]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2013/38362, 2013, A1 Location in patent: Page/Page column 75
[11]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2013/245002, 2013, A1 Location in patent: Paragraph 0700
[12]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2013/324526, 2013, A1 Location in patent: Paragraph 0456; 0457
[13]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN105968115, 2016, A Location in patent: Paragraph 0830-0832
[14]Lagnonx, David; Delort, Estelle; Douat-Casassus, Celine; Esposito, Annamaria; Reymond, Jean-Louis [Chemistry - A European Journal, 2004, vol. 10, # 5, p. 1215 - 1226]

2
[ 24306-33-0 ]
[ 13669-57-3 ]

Reference： [1]Patent: WO2012/107500,2012,A1
[2]Patent: WO2013/38362,2013,A1
[3]Patent: US2013/245002,2013,A1
[4]Patent: US2013/324526,2013,A1

3
[ 24306-33-0 ]
[ 727650-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: bromine; pyridine / tetrachloromethane / 3 h / 0 - 90 °C 2: potassium carbonate; water / methanol / 2 h / 20 °C 3: potassium carbonate / acetone / 20 °C 4: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
	Multi-step reaction with 5 steps 1: pyridine; bromine / tetrachloromethane / 3 h / 0 - 90 °C 2: potassium carbonate; water / methanol / 1 h / 20 °C 3: potassium carbonate / acetone / 20 °C 4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/38362, 2013, A1
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2013/245002, 2013, A1

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H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 24306-33-0 ] {[proInfo.proName]}

Quality Control of [ 24306-33-0 ]

Related Doc. of [ 24306-33-0 ]

Product Details of [ 24306-33-0 ]

Safety of [ 24306-33-0 ]

Application In Synthesis of [ 24306-33-0 ]

[ 24306-33-0 ] Synthesis Path-Upstream 1~1

[ 24306-33-0 ] Synthesis Path-Downstream 1~3

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Health hazards

Environmental hazards

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