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

HRID 1784620Notes

Reaction equation

HRID 1784620 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:33]=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[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:30]=[C:28]([C:27]5[CH:32]=[CH:33][C:24]([NH2:23])=[N:25][CH:26]=5)[N:29]=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 178513347HCID 178513347, compound

Product 1

HCID 160682505-{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 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 (27 mg, 13%). MS (ISP) 423.3 [(M+H)+]; mp 258° 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 (27 mg, 13%)

Sources & evidence

ORD record
ord-2ff99612bc454e7a8ded31e1b1598abe
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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