Piperidinium acetate → HCID 178518174, compound

HRID 1620789Notes

Reaction equation

HRID 1620789 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[F:24][C:25]1([F:39])[CH2:30][C@@H:29]([NH:31][C:32]2[CH2:36][S:35][C:34](=[O:37])[N:33]=2)[C@H:28]([OH:38])[CH2:27][CH2:26]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:36]2/[C:32]([NH:31][C@@H:29]3[CH2:30][C:25]([F:24])([F:39])[CH2:26][CH2:27][C@H:28]3[OH:38])=[N:33][C:34](=[O:37])[S:35]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518175HCID 178518175, compound

Product 1

HCID 178518174HCID 178518174, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (777 mg) in 2-propanol (5 mL) were added 4-[trans-(5,5-difluoro-2-hydroxycyclohexyl)amino]-1,3-thiazol-2(5H)-one (860 mg) and piperidinium acetate (339 mg). The reaction mixture was stirred at 75° C. overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (941 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-c6a7560789e540de923cc066b25f14bd
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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