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

HRID 418234Notes

Reaction equation

HRID 418234 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]([OH:20])=O)=[CH:16][N:17]=3)[CH:14]=2)=[CH:5][CH:4]=1.[NH2:23][C:24]1[CH:29]=[C:28]([C:30]([NH:32]O)=[NH:31])[CH:27]=[CH:26][N:25]=1>>[F:22][C:2]([F:21])([F:1])[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:20][N:32]=[C:30]([C:28]5[CH:27]=[CH:26][N:25]=[C:24]([NH2:23])[CH:29]=5)[N:31]=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 1785133752-amino-N'-hydroxypyridine-4-carboximidamide

Product 1

HCID 160683614-{5-[6-(4-Trifluoromethyl-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-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography on silica gel (dichloromethane/MeOH 16:1)) and crystallization (MeOH/dichloromethane/hexane) as an off-white solid (80 mg, 38%). MS (EI) 422.9 [(M)+]; mp 280° C.

Workup

  1. customObtained
  2. customafter purification by column chromatography on silica gel (dichloromethane/MeOH 16:1)) and
  3. customcrystallization (MeOH/dichloromethane/hexane) as an off-white solid (80 mg, 38%)

Sources & evidence

ORD record
ord-eaf25aaadb3045409eb01373a648b46c
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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