Piperidinium acetate → (2S)-2-[[(5Z)-5-[[1-[[2,4-bis(trifluoromethyl)phenyl]methyl]piperidin-4-yl]methylidene]-2-oxo-1,3-thiazol-4-yl]amino]-3-hydroxy-N,N,3-trimethylbutanamide

HRID 1620740Notes

Reaction equation

[OH:1][C:2]([CH3:17])([CH3:16])[C@@H:3]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[NH:4][C:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]=1.[F:18][C:19]([F:40])([F:39])[C:20]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:21]=1[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25][CH2:24]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:40][C:19]([F:18])([F:39])[C:20]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:21]=1[CH2:22][N:23]1[CH2:28][CH2:27][CH:26](/[CH:29]=[C:9]2/[C:5]([NH:4][C@H:3]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[C:2]([OH:1])([CH3:17])[CH3:16])=[N:6][C:7](=[O:10])[S:8]/2)[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-hydroxy-N,N-dimethyl-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-L-valinamide (300 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (392 mg) in 2-propanol (5 mL) was added piperidinium acetate (168 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 (170 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-f263ce5330384d6e87af6e2e2d82512b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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