Isopropanol → HCID 57970099, compound

HRID 1666642Notes

Reaction equation

HRID 1666642 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7](Cl)[CH:6]=1)=[O:4].Cl.[NH2:18][C@H:19]1[CH2:23][CH2:22][N:21]([C:24](=[O:37])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)[CH2:20]1.C(N(CC)CC)C.C(O)(C)C>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:16])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24](=[O:37])[CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=3)[CH2:20]2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 430827022-chloro-N,N-dimethylquinoline-4-carboxamideHCID 86636479(S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

Product 1

HCID 57970099HCID 57970099, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

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. washwashed with 1 M aqueous sodium hydroxide
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe desiccant was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=1:3−ethyl acetate)

Sources & evidence

ORD record
ord-cf62ed05c58e45ecb067d67b4122df3d
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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