1-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione → 3-(2,6-Dimethyl-pyridin-4-yl)-5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2054285Notes

Reaction equation

HRID 2054285 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]=[C:33]([CH3:35])[N:32]=[C:31]([CH3:36])[CH:30]=2)=[CH:27][NH:26][N:25]=1>>[CH3:35][C:33]1[CH:34]=[C:29]([C:28]2[CH:27]=[N:26][N:25]3[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([C:6]4[CH:7]=[CH:8][C:9]([C:10]([F:13])([F:12])[F:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=4)=[N:23][C:24]=23)[CH:30]=[C:31]([CH3:36])[N:32]=1

Participants

3

Reactant 2

HCID 865986761-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dioneHCID 178422939HCID 178422939, compound

Product 1

HCID 865986773-(2,6-Dimethyl-pyridin-4-yl)-5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 50%

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-(2,6-dimethyl-4-pyridinyl)-pyrazole [prepared from 4-cyanomethyl-2,6-dimethyl-pyridine, CAS No. 130138-46-4, as described in Bioorg. Med. Chem. Lett. 12 (2002) 3537-3541] (94 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (120 mg, 50%). MS (ISP) 481.4 [(M+H)+]; mp 257° C.

Sources & evidence

ORD record
ord-82d8972b7ee84ac1b173d1bd242ed292
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

Loading…