Piperidinium acetate → HCID 178456047, compound

HRID 1620649Notes

Reaction equation

HRID 1620649 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.[OH:24][CH2:25][C@H:26]([NH:29][C:30]1[CH2:34][S:33][C:32](=[O:35])[N:31]=1)[C:27]#[CH:28].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:34]2/[C:30]([NH:29][C@@H:26]([CH2:25][OH:24])[C:27]#[CH:28])=[N:31][C:32](=[O:35])[S:33]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178456046HCID 178456046, compound

Product 1

HCID 178456047HCID 178456047, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (135 mg) in 2-propanol (5 mL) were added (R)-4-[(1-hydroxybut-3-yn-2-yl)amino]thiazol-2(5H)-one (110 mg) and piperidinium acetate (59 mg). The reaction mixture was heated under reflux 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 (83 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  5. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-41e7cb705d93467e8f24362e7d2a7c1d
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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