3-Amino-4-cyano-5-cyanomethylpyrazole → 5-(4-Chloro-3-methyl-phenyl)-2-cyanomethyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2108413Notes

Reaction equation

HRID 2108413 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])=[C:22]([CH2:26][C:27]#[N:28])[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]=[C:22]([CH2:26][C:27]#[N:28])[C:23]([C:24]#[N:25])=[C:19]3[N:18]=2)=[CH:4][C:3]=1[CH3:17]

Participants

3

Reactant 2

HCID 951853-Amino-4-cyano-5-cyanomethylpyrazoleHCID 670009781,3-Butanedione, 1-(4-chloro-3-methylphenyl)-4,4,4-trifluoro-

Product 1

HCID 672134845-(4-Chloro-3-methyl-phenyl)-2-cyanomethyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 53%

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 commercially available 3-amino-4-cyano-5-cyanomethyl-pyrazole (74 mg, 0.5 mmol) according to general procedure B yielded the title compound as a light yellow solid (99 mg, 53%). MS (ISP) 376.1 [(M+H)+]; mp 238° C.

Sources & evidence

ORD record
ord-74715c74dc024281a3bd9917fcd14b65
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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