Dimethylformamide → 3-[4-(4-Fluoro-2-methylphenyl)-1-piperazinyl]-5-methyl-3-phenylisoxazole-4-carboxamide

HRID 840132Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[C:4]([CH3:14])[CH:3]=1.C(N(CC)C(C)C)(C)C.ClCCC[NH:28][C:29]([C:31]1[C:32]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:33][O:34][C:35]=1[CH3:36])=[O:30].CN(C)C=O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:32]3([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]([C:29]([NH2:28])=[O:30])=[C:35]([CH3:36])[O:34][NH:33]3)[CH2:10][CH2:9]2)=[C:4]([CH3:14])[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of 0.380 g of Compound 31A, 0.50 mL of N,N-diisopropylethylamine, 0.545 g of Compound 2B and 3 mL of N,N-dimethylformamide was heated at 120° C. for 5 h. The solution was diluted with water (60 mL) and extracted with dichloromethane (3×30 mL); the organic layer was washed with water (3×20 mL), dried (anhydrous sodium sulphate) and evaporated to dryness in vacuo. The residue was purified by flash chromatography (chloroform-2N methanolic ammonia 100:1) affording 0.373 g (43.7%) of the title compound as an ivory solid. M.p. 139-141° C.

Workup

extractionextracted with dichloromethane (3×30 mL)
washthe organic layer was washed with water (3×20 mL)
dry with materialdried (anhydrous sodium sulphate)
customevaporated to dryness in vacuo
customThe residue was purified by flash chromatography (chloroform-2N methanolic ammonia 100:1)

Sources & evidence

ORD record: ord-cc40e651339f4e4da172e78020c98c50
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365591B1

Reaction notes

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