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

HRID 418253Notes

Reaction equation

HRID 418253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21](O)=[O:22])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([NH:33]O)=[NH:32])=[CH:27][N:26]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21]4[O:22][N:33]=[C:31]([C:28]5[CH:27]=[N:26][C:25]([NH2:24])=[N:30][CH:29]=5)[N:32]=4)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 532122235-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513389HCID 178513389, compound

Product 1

HCID 160680255-{5-[5-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 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 (165 mg, 72%). MS (EI) 458.1 [(M)+]; mp 268° 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 (165 mg, 72%)

Sources & evidence

ORD record
ord-e9e308a9f85546dda992067e986ee2a7
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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