6-(4-Trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid → 3-{5-[6-(4-Trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-benzenesulfonamide

HRID 418227Notes

Reaction equation

HRID 418227 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18](O)=[O:19])=[CH:16][N:17]=3)[CH:14]=2)=[CH:5][CH:4]=1.O[NH:24][C:25](=[NH:36])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([S:32](=[O:35])(=[O:34])[NH2:33])[CH:27]=1>>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]4[O:19][N:36]=[C:25]([C:26]5[CH:27]=[C:28]([S:32]([NH2:33])(=[O:34])=[O:35])[CH:29]=[CH:30][CH:31]=5)[N:24]=4)=[CH:16][N:17]=3)[CH:14]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 666501476-(4-Trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acidHCID 178513322HCID 178513322, compound

Product 1

HCID 160682473-{5-[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 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (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 (202 mg, 83%). MS (ISP) 486.3 [(M+H)+]; mp 288° C.

Workup

  1. customObtained after trituration
  2. customwith water and further purification
  3. customby crystallization (MeOH/diethyl ether) as an off-white solid (202 mg, 83%)

Sources & evidence

ORD record
ord-d6c0f5e14493472a9a0c6558ea31d561
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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