Hydrochloric Acid → HCID 86636482, compound

HRID 1666643Notes

Reaction equation

HRID 1666643 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)[CH2:17]2)[CH:6]=1)=[O:4].[ClH:36]>C(OCC)(=O)C>[ClH:36].[CH3:35][N:2]([CH3:1])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[CH2:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:27][CH:28]=3)[CH2:17]2)[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57970099HCID 57970099, compound

Product 1

HCID 86636482HCID 86636482, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-chloroquinoline-4-carboxylic acid dimethylamide (0.20 g), 1-((S)-3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride (0.13 g), triethylamine (95 mg), and isopropanol (0.85 mL) was heated at 130° C. in a microwave reaction apparatus for 1.5 h. The reaction mixture was diluted with chloroform, washed with 1 M aqueous sodium hydroxide, and then dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=1:3−ethyl acetate) to obtain 2-((S)-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-ylamino)quinoline-4-carboxylic acid dimethylamide (36 mg). (2) 2-((S)-1-(2-(4-Trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-ylamino)quinoline-4-carboxylic acid dimethylamide (36 mg) was dissolved in ethyl acetate, followed by addition of a solution (0.046 mL) of 4 M HCl in ethyl acetate. The mixture was concentrated under reduced pressure, and then the resulting residue was solidified with a mixed solvent of diisopropyl ether and chloroform to obtain the title compound (21 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-426c07c053cc4b5a9dce8f4fcdaf1b85
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

Loading…