Hydrochloric Acid → 1-((S)-3-(4-methylquinolin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

HRID 1666609Notes

Reaction equation

HRID 1666609 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18](=[O:31])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[CH2:14]2)[CH:3]=1.[ClH:32]>C(OCC)(=O)C>[ClH:32].[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18](=[O:31])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:22][CH:21]=3)[CH2:14]2)[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57970075HCID 57970075, compound

Product 1

HCID 866364811-((S)-3-(4-methylquinolin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-chloro-4-methylquinoline (0.30 g), 1-((S)-3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride (0.60 g), N,N-diisopropylethylamine (0.74 mL), and n-butanol (1.5 mL) was heated at 140° C. in a sealed tube for 23 h. The reaction mixture was diluted with chloroform and saturated aqueous sodium hydrogencarbonate, and then the aqueous layer was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=1:1) to obtain 1-((S)-3-(4-methylquinolin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (0.24 g). (2) 1-((S)-3-(4-Methylquinolin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (0.24 g) was dissolved in ethyl acetate (2.5 mL), followed by addition of a solution (0.28 mL) of 4 M HCl in ethyl acetate, the mixture was stirred at room temperature for 2 h, concentrated under reduced pressure, and then solidified with diethyl ether to obtain the title compound (0.24 g).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e585358b8f6641e9b07b41dab1522d22
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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