N-hydroxy-4-sulfamoylbenzene-1-carboximidamide → 4-{5-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-benzenesulfonamide

HRID 418185Notes

Reaction equation

HRID 418185 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[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.O[NH:24][C:25](=[NH:36])[C:26]1[CH:31]=[CH:30][C:29]([S:32](=[O:35])(=[O:34])[NH2:33])=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([C:20]4[O:22][N:36]=[C:25]([C:26]5[CH:27]=[CH:28][C:29]([S:32]([NH2:33])(=[O:34])=[O:35])=[CH:30][CH:31]=5)[N:24]=4)=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 666504695-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 160687664-{5-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-benzenesulfonamide

Procedure

The title compound was prepared from 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.28) (157 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (dichloromethane/MeOH/NH4OH) and crystallization (dichloromethane) as a light yellow solid (60 mg, 24%). MS (EI) 492.1 [(M)+]; mp 260° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby column chromatography (dichloromethane/MeOH/NH4OH) and crystallization (dichloromethane) as a light yellow solid (60 mg, 24%)

Sources & evidence

ORD record
ord-02642eee293f4cff816074bce9a7ebc3
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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