1-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione → 5-(3-Ethoxy-4-trifluoromethyl-phenyl)-3-(2-methyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2108461Notes

Reaction equation

HRID 2108461 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14](=O)[CH2:15][C:16](=O)[C:17]([F:20])([F:19])[F:18])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH3:2].[NH2:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=2)=[CH:27][NH:26][N:25]=1>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14]2[CH:15]=[C:16]([C:17]([F:20])([F:19])[F:18])[N:25]3[N:26]=[CH:27][C:28]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)=[C:24]3[N:23]=2)[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH3:2]

Participants

3

Reactant 2

HCID 865986761-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dioneHCID 178422940HCID 178422940, compound

Product 1

HCID 865986785-(3-Ethoxy-4-trifluoromethyl-phenyl)-3-(2-methyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 49%

Procedure

Reaction of 1-(3-ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (164 mg, 0.5 mmol), prepared from 3-ethoxy-4-trifluoromethyl-acetophenone (synthesis: see part acetophenone derivatives) according to general procedure A, and 3-amino-4-(2-methyl-4-pyridinyl)-pyrazole [prepared from 4-cyanomethyl-2-methyl-pyridine, as described in Bioorg. Med. Chem. Lett. 12 (2002) 3537-3541] (87 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (113 mg, 49%). MS (ISP) 467.4 [(M+H)+]; mp 226° C.

Sources & evidence

ORD record
ord-41856fb6450f4206805b7dd96a10b3d1
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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