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

HRID 840120Notes

Reaction equation

HRID 840120 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][C:31]([F:34])=[CH:30][C:29]=2[O:35][CH2:36][C:37]([F:40])([F:39])[F:38])[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[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[O:35][CH2:36][C:37]([F:38])([F:40])[F:39])[CH2:24][CH2:23]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 234479111-(3-Aminopropyl)-4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine

Product 1

HCID 234479163-(2,6-Dichlorophenyl)-N-[3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]pro-pyl]-5-methylisoxazole-4-carboxamideYield 38%

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-methyl-isoxazole-4-carboxylic acid and Compound 8B 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 (38%) 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-6fd00cdf426b421f9620486f784e2ccc
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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