Piperidinium acetate → HCID 178448315, compound

HRID 1620772Notes

Reaction equation

[CH3:1][CH:2]([CH3:19])[C@H:3]([NH:12][C:13]1[CH2:17][S:16][C:15](=[O:18])[N:14]=1)[C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].[F:20][C:21]([F:42])([F:41])[C:22]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:23]=1[CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27][CH2:26]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:42][C:21]([F:20])([F:41])[C:22]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:23]=1[CH2:24][N:25]1[CH2:30][CH2:29][CH:28](/[CH:31]=[C:17]2/[C:13]([NH:12][C@H:3]([C:4]([N:6]3[CH2:7][CH2:8][O:9][CH2:10][CH2:11]3)=[O:5])[CH:2]([CH3:19])[CH3:1])=[N:14][C:15](=[O:18])[S:16]/2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-{[(2S)-3-methyl-1-(morpholin-4-yl)-1-oxobutan-2-yl]amino}-1,3-thiazol-2(5H)-one (371 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (441 mg) in 2-propanol (10 mL) was added piperidinium acetate (189 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (416 mg).

Workup

customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record: ord-29a17652d31847dcbd1fa7f544e60b9a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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