1,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro- → 5-(4-Chloro-3-methyl-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2108433Notes

Reaction equation

HRID 2108433 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:17].[NH2:18][C:19]1[C:23]([C:24]2[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[CH:25]=2)=[CH:22][NH:21][N:20]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:20]3[N:21]=[CH:22][C:23]([C:24]4[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[CH:25]=4)=[C:19]3[N:18]=2)=[CH:4][C:3]=1[CH3:17]

Participants

3

Reactant 2

HCID 670009781,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro-HCID 178422939HCID 178422939, compound

Product 1

HCID 112585725-(4-Chloro-3-methyl-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 46%

Procedure

Reaction of 1-(4-chloro-3-methyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (132 mg, 0.5 mmol), prepared from commercially available 4-chloro-3-methyl-acetophenone according to general procedure A, and 3-amino-4-(2,6-dimethyl-4-pyridinyl)-pyrazole [prepared from 4-cyanomethyl-2,6-dimethyl-pyridine, see part synthesis of amino-pyrazole derivatives] (94 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (95 mg, 46%). MS (ISP) 417.2 [(M+H)+]; mp 254° C.

Sources & evidence

ORD record
ord-566b4b2c27e54e11aa7b969d6490f29c
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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