N-hydroxy-4-sulfamoylbenzene-1-carboximidamide → 4-{5-[8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-benzenesulfonamide

HRID 418190Notes

Reaction equation

HRID 418190 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[C:4]2[N:5]([C:19]([C:22](O)=[O:23])=[CH:20][N:21]=2)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:8]=1.O[NH:28][C:29](=[NH:40])[C:30]1[CH:35]=[CH:34][C:33]([S:36](=[O:39])(=[O:38])[NH2:37])=[CH:32][CH:31]=1>>[F:26][C:2]([F:1])([F:25])[C:3]1[C:4]2[N:5]([C:19]([C:22]3[O:23][N:40]=[C:29]([C:30]4[CH:31]=[CH:32][C:33]([S:36]([NH2:37])(=[O:38])=[O:39])=[CH:34][CH:35]=4)[N:28]=3)=[CH:20][N:21]=2)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 866116268-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 160683634-{5-[8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-benzenesulfonamide

Procedure

The title compound was prepared from 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.32) (187 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 flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (143 mg, 52%). MS (EI) 553.1 [(M)+]; mp 292° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby flash chromatography (ethyl acetate/heptane) and crystallization (dichloromethane) as a yellow solid (143 mg, 52%)

Sources & evidence

ORD record
ord-0f8b22172efb45f8a24ee4c6dc9b4fb2
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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