4-Isoxazolecarbonyl chloride, 3-(2-chlorophenyl)-5-methyl- → 3-(2-Chlorophenyl)-5-methyl-n-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl]-isoxazole-4-carboxamide

HRID 840122Notes

Reaction equation

HRID 840122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13](Cl)=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][C:35]([F:38])([F:37])[F:36])[CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]([NH:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH2:34][C:35]([F:37])([F:38])[F:36])[CH2:25][CH2:26]2)=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1

Participants

3

Reactant 2

HCID 965904-Isoxazolecarbonyl chloride, 3-(2-chlorophenyl)-5-methyl-HCID 105674903-{4-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazin-1-yl}propylamine

Product 1

HCID 99588303-(2-Chlorophenyl)-5-methyl-n-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl]-isoxazole-4-carboxamideYield 67.2%

Procedure

The title compound was synthesised according to the procedure described in Example 8 but using 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride instead of the crude 3-(4-fluorophenyl)isoxazole-4-carbonyl chloride and Compound 12B instead of Compound 8B. Washing the reaction mixture with 2 N sodium hydroxide, followed by the usual work-up and purification by flash chromatography (chloroform-2 N ammonia in methanol 100:3) afforded the title compound (67.2%) as an oil.

Workup

  1. customThe title compound was synthesised
  2. washWashing the reaction mixture with 2 N sodium hydroxide
  3. customfollowed by the usual work-up and purification by flash chromatography (chloroform-2 N ammonia in methanol 100:3)

Sources & evidence

ORD record
ord-3df818bfec0d4ac7b0dbecf936a972c2
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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