7-Difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid → HCID 16067516, compound

HRID 418208Notes

Reaction equation

HRID 418208 reaction equation
[F:1][CH:2]([F:25])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12](O)=[O:13])=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:4]=1.O[NH:27][C:28]([C:30]1[S:31][C:32]([S:35](=[O:38])(=[O:37])[NH2:36])=[CH:33][CH:34]=1)=[NH:29]>>[F:25][CH:2]([F:1])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]3[O:13][N:29]=[C:28]([C:30]4[S:31][C:32]([S:35]([NH2:36])(=[O:38])=[O:37])=[CH:33][CH:34]=4)[N:27]=3)=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][CH:16]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 666502687-Difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513361HCID 178513361, compound

Product 1

HCID 16067516HCID 16067516, compound

Procedure

The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) (179 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (200 mg, 74%). MS (EI) 542.0 [(M+H)+]; mp 278° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (200 mg, 74%)

Sources & evidence

ORD record
ord-fd136ec248f04eb0bbb8fbf654cddb7d
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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