Aniline → 8-(1,3-oxazol-5-yl)-N-phenyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 931013Notes

Reaction equation

HRID 931013 reaction equation
[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)=[CH:4][N:3]=[CH:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(N(CC)CC)C>[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([NH:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[O:21])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:11]=2)=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1183789628-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 1183790298-(1,3-oxazol-5-yl)-N-phenyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamideYield 43.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (150 mg) in DMF (2 mL) were added HATU (230 mg) and triethylamine (0.091 mL), and the mixture was stirred at room temperature for 2 min. To the reaction mixture was added aniline (51.7 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (82 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7bdc48c26e604c4d8e9f0f6498173de6
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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