3-Sulfamoylbenzoic acid → 3-{3-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-5-yl}-benzenesulfonamide

HRID 418192

Reaction equation

HRID 418192 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][N:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:10][C:9]=12)=[NH:4].[S:28]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](O)=O)(=[O:31])(=[O:30])[NH2:29]>>[F:17][C:14]([F:15])([F:16])[C:13]1[N:8]2[N:7]=[CH:6][C:5]([C:3]3[N:4]=[C:35]([C:34]4[CH:33]=[C:32]([S:28]([NH2:29])(=[O:31])=[O:30])[CH:40]=[CH:39][CH:38]=4)[O:1][N:2]=3)=[C:9]2[N:10]=[C:11]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 2293523-Sulfamoylbenzoic acidHCID 178513391HCID 178513391, compound

Product 1

HCID 160688783-{3-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-5-yl}-benzenesulfonamide

Procedure

The title compound was prepared from N-hydroxy-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxamidine (example B.1) (195 mg, 0.5 mmol) and commercially available 3-sulfamoyl-benzoic acid (101 mg, 0.5 mmol) according to general procedure II. Obtained after purification by flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (144 mg, 52%). MS (ISN) 553.3 [(M−H)−]; mp 285° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (144 mg, 52%)

Sources & evidence

ORD record
ord-04e19f8ec2814bf989c7dde574feb2bf
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Linked notes

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