3-amino-5-methyl-1H-pyrazole-4-carbonitrile → 5-(3-Chloro-4-fluoro-phenyl)-2-methyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2054236Notes

Reaction equation

HRID 2054236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:18][C:19]1[C:23]([C:24]#[N:25])=[C:22]([CH3:26])[NH:21][N:20]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:20]3[N:21]=[C:22]([CH3:26])[C:23]([C:24]#[N:25])=[C:19]3[N:18]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 2274603-amino-5-methyl-1H-pyrazole-4-carbonitrileHCID 129216971-(3-Chloro-4-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 672132445-(3-Chloro-4-fluoro-phenyl)-2-methyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 69%

Procedure

Reaction of 1-(3-chloro-4-fluoro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (269 mg, 1.0 mmol), prepared from commercially available 3-chloro-4-fluoro-acetophenone according to general procedure A, and commercially available 3-amino-4-cyano-5-methyl-pyrazole (122 mg, 1.0 mmol) according to general procedure B yielded the title compound as a light yellow solid (243 mg, 69%). MS (ISP) 355.0 [(M+H)+]; mp 196° C.

Sources & evidence

ORD record
ord-4bcb9b674ffc463f820022df92e9d2ed
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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