Piperidinium acetate → HCID 178484592, compound

HRID 1620775Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[C:3](=[O:17])[C@H:4]([CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:19][C:20]([F:41])([F:40])[C:21]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([CH:30]=O)[CH2:26][CH2:25]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:41][C:20]([F:19])([F:40])[C:21]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][CH:27](/[CH:30]=[C:10]2/[C:6]([NH:5][C@H:4]([C:3]([N:2]([CH3:18])[CH3:1])=[O:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N,N-dimethyl-3-(methylsulfonyl)-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-L-alaninamide (150 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (173 mg) in 2-propanol (5 mL) was added piperidinium acetate (74 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 (55 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-8f44eb8313c0444d95a71e9219a5856d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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