Potassium tert-butoxide → HCID 178518076, compound

HRID 1620497Notes

Reaction equation

HRID 1620497 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.[CH:24]1([CH2:27][NH:28][C:29]2[CH2:33][S:32][C:31](=[O:34])[N:30]=2)[CH2:26][CH2:25]1.CC(C)([O-])C.[K+]>C(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:33]2/[C:29]([NH:28][CH2:27][CH:24]3[CH2:25][CH2:26]3)=[N:30][C:31](=[O:34])[S:32]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518077HCID 178518077, compound

Product 1

HCID 178518076HCID 178518076, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (200 mg) and 4-[(cyclopropylmethyl)amino]-1,3-thiazol-2(5H)-one (100 mg) were suspended in ethanol (3 mL), potassium tert-butoxide (66.1 mg) was added, and the reaction mixture was stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (180 mg).

Workup

  1. concentrationThe reaction mixture was concentrated 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-d425e51136c04345ac28474b9e2e9447
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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