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

HRID 1801808Notes

Reaction equation

HRID 1801808 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:18]([C:21]([OH:23])=O)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:7]=1.O[NH:25][C:26](=[NH:37])[C:27]1[CH:32]=[CH:31][C:30]([S:33](=[O:36])(=[O:35])[NH2:34])=[CH:29][CH:28]=1>>[CH3:1][C:2]1[C:3]2[N:4]([C:18]([C:21]3[O:23][N:37]=[C:26]([C:27]4[CH:28]=[CH:29][C:30]([S:33]([NH2:34])(=[O:35])=[O:36])=[CH:31][CH:32]=4)[N:25]=3)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 666503088-Methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 160684594-{5-[8-Methyl-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-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 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 trituration with water and further purification by crystallization (MeOH/diethyl ether) as an off-white solid (146 mg, 58%). MS (ISP) 500.3 [(M+H)+]; mp 290° C.

Workup

  1. customObtained after trituration
  2. customwith water and further purification
  3. customby crystallization (MeOH/diethyl ether) as an off-white solid (146 mg, 58%)

Sources & evidence

ORD record
ord-9138ff4eba854a38aa061dd07edfddb8
Source dataset
uspto-grants-2013_01
Patent number
US08349844B2

Reaction notes

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