1,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro- → 5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2054227Notes

Reaction equation

HRID 2054227 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]#[N:25])=[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]#[N:25])=[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 178510443HCID 178510443, compound

Product 1

HCID 114391115-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 38%

Procedure

Reaction of 1-(4-chloro-3-methyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (264 mg, 1.0 mmol), prepared from commercially available 4-chloro-3-methyl-acetophenone according to general procedure A, and 3-amino-4-cyano-pyrazole (108 mg, 1.0 mmol) according to general procedure B yielded the title compound as an off-white solid (128 mg, 38%). MS (ISP) 337.1 [(M+H)+]; mp 216° C.

Sources & evidence

ORD record
ord-6fca80d1e0184f73b613ff06c0bd1749
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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