Piperidinium acetate → HCID 178484595, compound

HRID 1620750Notes

Reaction equation

HRID 1620750 reaction equation
[CH:1]1([C@H:4]([NH:10][C:11]2[CH2:15][S:14][C:13](=[O:16])[N:12]=2)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])[CH2:3][CH2:2]1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:39][C:18]([F:17])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25](/[CH:28]=[C:15]2/[C:11]([NH:10][C@@H:4]([CH:1]3[CH2:3][CH2:2]3)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])=[N:12][C:13](=[O:16])[S:14]/2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178484593HCID 178484593, compound

Product 1

HCID 178484595HCID 178484595, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S)-2-cyclopropyl-N,N-dimethyl-2-[(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)amino]ethanamide (796 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1018 mg) in 2-propanol (10 mL) was added piperidinium acetate (479 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 (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (1111 mg).

Workup

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

Sources & evidence

ORD record
ord-fc6bc6ad124d470f825c5af236721c41
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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