6-(4-Chloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid → 5-{5-[6-(4-Chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-thiophene-2-sulfonic Acid Amide

HRID 418229Notes

Reaction equation

HRID 418229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.O[NH:21][C:22]([C:24]1[S:25][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:27][CH:28]=1)=[NH:23]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]4[O:19][N:23]=[C:22]([C:24]5[S:25][C:26]([S:29]([NH2:30])(=[O:32])=[O:31])=[CH:27][CH:28]=5)[N:21]=4)=[CH:15][N:16]=3)[CH:13]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 666503596-(4-Chloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acidHCID 178513361HCID 178513361, compound

Product 1

HCID 160682495-{5-[6-(4-Chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-thiophene-2-sulfonic Acid Amide

Procedure

The title compound was prepared from 6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.36) (136 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purification by crystallization (heptane/diethyl ether) as an off-white solid (160 mg, 70%). MS (ISP) 458.2 [(M+H)+]; mp 263° C.

Workup

  1. customObtained after trituration
  2. customwith water and further purification
  3. customby crystallization (heptane/diethyl ether) as an off-white solid (160 mg, 70%)

Sources & evidence

ORD record
ord-5823e8c2a47d4ca48923d0ff294e0225
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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