Ammonia → 4-(4-Fluorophenyl)-5-[2-[4-[(3-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-1,3-thiazole-2-carboxamide
Reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][C:23](=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[CH2:22][CH2:21]2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:10]=1)=O)C.[NH3:34]>C(O)C>[C:4]([C:6]1[S:7][C:8]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][C:23](=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[CH2:24][CH2:25]2)=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[N:10]=1)(=[O:3])[NH2:34]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
315 mg of 2-ethoxycarbonyl-4-(4-fluorophenyl)-5-[2-[4-(3-fluorobenzylidene)piperidin-1-yl]ethyl]thiazole and 0.05 ml of 28% aqueous ammonia were stirred in 1.5 ml of ethanol for 3 days. To the mixture was added 0.50 ml of 28% aqueous ammonia to carry out additional 3 days of reaction. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by a flash column chromatography (Wako Gel C200 (manufactured by Wako Pure Chemical Industries), eluant: hexane-ethyl acetate=3:1-1:1) and recrystallized from ethanol to obtain 201 mg of 2-carbamoyl-4-(4-fluorophenyl)-5-[2-[4-(3-fluorobenzylidene)piperidin-1-yl]ethyl]thiazole.
Workup
- customto carry out additional 3 days of reaction
- concentrationThe reaction solution was concentrated under reduced pressure
- customthe resulting residue was purified by a flash column chromatography (Wako Gel C200 (manufactured by Wako Pure Chemical Industries), eluant: hexane-ethyl acetate=3:1-1:1)
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-39fb47b1a04a4411b5892a880caefcd3
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166033
Reaction notes
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