3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride → 3-(2-Chloro-6-fluorophenyl)-5-methyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazi-nyl]propyl]isoxazole-4-carboxamide

HRID 1840294Notes

Reaction equation

HRID 1840294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](Cl)=[O:15])=[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:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[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:15])=[C:12]([CH3:17])[O:11][N:10]=1

Participants

3

Reactant 2

HCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 105674903-{4-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazin-1-yl}propylamine

Product 1

HCID 234478933-(2-Chloro-6-fluorophenyl)-5-methyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazi-nyl]propyl]isoxazole-4-carboxamideYield 92%

Procedure

The title compound was synthesised according to the procedure described in Example 8 but using 3-(2-chloro-6-fluorophenyl)-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 (92%) 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-64d4a8fb2327441c926ec82cc22b0b1a
Source dataset
uspto-grants-2004_01
Patent number
US06680319B2

Reaction notes

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