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

HRID 418204Notes

Reaction equation

HRID 418204 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]([OH:14])=O)=[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:28][C:29]([C:31]1[S:32][C:33]([S:36](=[O:39])(=[O:38])[NH2:37])=[CH:34][CH:35]=1)=[NH:30]>>[F:26][C:2]([F:25])([F:1])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]3[O:14][N:30]=[C:29]([C:31]4[S:32][C:33]([S:36]([NH2:37])(=[O:39])=[O:38])=[CH:34][CH:35]=4)[N:28]=3)=[C:7]2[N:6]=[C:5]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 866071127-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513361HCID 178513361, compound

Product 1

HCID 160690865-{5-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-thiophene-2-sulfonic acid amide

Procedure

The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 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 an off-white solid (130 mg, 46%). MS (ISN) 558.0 [(M−H)−]; mp 276° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as an off-white solid (130 mg, 46%)

Sources & evidence

ORD record
ord-d048776c10ac4fc9913e9002d8237478
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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