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

HRID 418236Notes

Reaction equation

HRID 418236 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([F:16])[F:15])[N:11]3[N:17]=[CH:18][C:19]([C:20]([OH:22])=O)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[CH:26][N:25]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([F:15])[F:16])[N:11]3[N:17]=[CH:18][C:19]([C:20]4[O:22][N:30]=[C:28]([C:27]5[CH:32]=[CH:33][C:24]([NH2:23])=[N:25][CH:26]=5)[N:29]=4)=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 666503265-(4-Chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513347HCID 178513347, compound

Product 1

HCID 160677025-{5-[5-(4-Chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 5-(4-chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.3) (162 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 (114 mg, 52%). MS (ISP) 440.2 [(M+H)+]; mp 254° 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 (114 mg, 52%)

Sources & evidence

ORD record
ord-3f220b00dc994b8bafce7032aadc2dc0
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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