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}-pyridin-2-ylamine

HRID 418231Notes

Reaction equation

HRID 418231 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.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27]O)=[NH:26])=[CH:23][N:22]=1>>[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:27]=[C:25]([C:24]5[CH:29]=[CH:30][C:21]([NH2:20])=[N:22][CH:23]=5)[N:26]=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 178513347HCID 178513347, compound

Product 1

HCID 160682515-{5-[6-(4-Chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

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 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetate) and further purification by crystallization (MeOH/diethyl ether) as a white solid (34 mg, 17%). MS (ISP) 389.3 [(M+H)+]; mp 273° C.

Workup

  1. customObtained after flash chromatography
  2. customon silica gel (ethyl acetate) and further purification
  3. customby crystallization (MeOH/diethyl ether) as a white solid (34 mg, 17%)

Sources & evidence

ORD record
ord-342ad29f7e9e45448098f3e24bbc1c57
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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