Trifluoroacetic acid → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide

HRID 1510271Notes

Reaction equation

HRID 1510271 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24]=[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:26][C:27]=3[C:28]([F:31])([F:30])[F:29])=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[N:24]=[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:26][C:27]=3[C:28]([F:29])([F:30])[F:31])=[O:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667383654-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 529371572-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (19.2 g, 37.3 mmol) in dichloromethane (250 mL) was added trifluoroacetic acid (30 mL). The solution was stirred at room temperature for 3 hrs. Solvents were evaporated and the residue was diluted with ethyl acetate (600 mL). The mixture was neutralized with 1N sodium hydroxide solution (final PH >10). The organic layer was separated and washed with water and brine. After the evaporation of solvents, a pale yellow solid was obtained as 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide (15.3 g, 99%). LC-MS calcd for C22H20F3N3O2 (m/e) 415, obsd 416 (M+H).

Workup

  1. customSolvents were evaporated
  2. additionthe residue was diluted with ethyl acetate (600 mL)
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. customAfter the evaporation of solvents

Sources & evidence

ORD record
ord-30ca264a58c74d6c85fb9ab5542a00c2
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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