5-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid → 5-{5-[5-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

HRID 418240Notes

Reaction equation

HRID 418240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]3[N:19]=[CH:20][C:21]([C:22](O)=[O:23])=[C:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([NH:32]O)=[NH:31])=[CH:28][N:27]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([C:15]([F:16])([F:18])[F:17])[N:12]3[N:19]=[CH:20][C:21]([C:22]4[O:23][N:32]=[C:30]([C:29]5[CH:34]=[CH:35][C:26]([NH2:25])=[N:27][CH:28]=5)[N:31]=4)=[C:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 666502945-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513347HCID 178513347, compound

Product 1

HCID 160678035-{5-[5-(3,4-Dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.9) (188 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 (35 mg, 14%). MS (ISP) 492.0 [(M+H)+]; mp 289° C.

Workup

  1. customObtained after flash chromatography
  2. customon silica gel (ethyl acetate/heptane) and further purification
  3. customby crystallization (dichloromethane/hexane) as a yellow solid (35 mg, 14%)

Sources & evidence

ORD record
ord-05f3839161a04c88aeeb802d00cb7e4c
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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