4-Isoxazolecarboxylic acid, 3-(2,6-dichlorophenyl)-5-methyl- → 3-(2,6-Dichlorophenyl)-5-methyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]pro-pyl]isoxazole-4-carboxamide

HRID 840123Notes

Reaction equation

HRID 840123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[O:11][N:10]=1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][C:36]([F:39])([F:38])[F:37])[CH2:24][CH2:23]1>>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([C:14]([NH:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH2:35][C:36]([F:38])([F:39])[F:37])[CH2:26][CH2:27]2)=[O:16])=[C:12]([CH3:17])[O:11][N:10]=1

Participants

3

Reactant 2

HCID 775214-Isoxazolecarboxylic acid, 3-(2,6-dichlorophenyl)-5-methyl-HCID 105674903-{4-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazin-1-yl}propylamine

Product 1

HCID 234478843-(2,6-Dichlorophenyl)-5-methyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]pro-pyl]isoxazole-4-carboxamideYield 75%

Procedure

The title compound was synthesised according to the procedure described in Example 1 but using 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid instead of 3-phenyl-5-methyliso-xazole-4-carboxylic acid and Compound 12B instead of Compound 1B. Extraction with diethyl ether followed by purification by flash chromatography (chloroform-2 N ammonia in methanol 100:3) afforded the title compound (75%) as an oil.

Workup

  1. customThe title compound was synthesised
  2. extractionExtraction with diethyl ether
  3. customfollowed by purification by flash chromatography (chloroform-2 N ammonia in methanol 100:3)

Sources & evidence

ORD record
ord-3b1aea449f6340f683beff946f256683
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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