4,4,4-Trifluoro-1-[3-(trifluoromethyl)phenyl]butane-1,3-dione → 5-(3-Trifluoromethyl-phenyl)-3-pyridin-4-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2054254Notes

Reaction equation

HRID 2054254 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:7][CH:8]=1.[NH2:20][C:21]1[C:25]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:24][NH:23][N:22]=1>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:22]3[N:23]=[CH:24][C:25]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)=[C:21]3[N:20]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 162279574,4,4-Trifluoro-1-[3-(trifluoromethyl)phenyl]butane-1,3-dioneHCID 178509259HCID 178509259, compound

Product 1

HCID 113618185-(3-Trifluoromethyl-phenyl)-3-pyridin-4-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 47%

Procedure

Reaction of 1-(3-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (142 mg, 0.5 mmol), prepared from commercially available 3-trifluoromethyl-acetophenone according to general procedure A, and 3-amino-4-(4-pyridinyl)-pyrazole [CAS No. 216661-87-9; prepared from 4-cyanomethyl-pyridine as described in Bioorg. Med. Chem. Lett. 12 (2002) 3537-3541] (80 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (95 mg, 47%). MS (ISP) 409.2 [(M+H)+]; mp 241° C.

Sources & evidence

ORD record
ord-f54c07013b76467386b17ae8e89fbc82
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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