5-(3-Ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid → 5-{5-[5-(3-Ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo [1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:17]3[N:24]=[CH:25][C:26]([C:27](O)=[O:28])=[C:16]3[N:15]=2)[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH3:2].[NH2:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([NH:37]O)=[NH:36])=[CH:33][N:32]=1>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[N:17]3[N:24]=[CH:25][C:26]([C:27]4[O:28][N:37]=[C:35]([C:34]5[CH:39]=[CH:40][C:31]([NH2:30])=[N:32][CH:33]=5)[N:36]=4)=[C:16]3[N:15]=2)[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:11])[F:12])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.11) (210 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetate/heptane) and further purification by crystallization (dichloromethane/hexane) as a yellow solid (120 mg, 45%). MS (ISP) 536.3 [(M+H)+]; mp 263° C.
Workup
- customObtained after flash chromatography
- customon silica gel (ethyl acetate/heptane) and further purification
- customby crystallization (dichloromethane/hexane) as a yellow solid (120 mg, 45%)
Sources & evidence
- ORD record
- ord-2cc2eca7d0e042d59754c88fc047b514
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093263B2
Reaction notes
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