3,4,5-Trifluoroaniline → Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[(3,4,5-trifluorophenyl)amino]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398232Notes

Reaction equation

HRID 1398232 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].Cl[C:12]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][C:30]([CH3:32])=[N:29][CH:28]=4)=[C:23]([O:33][CH3:34])[CH:22]=3)=[N:19][N:20]=[C:13]12>C(=O)([O-])O.[Na+]>[CH3:34][O:33][C:23]1[CH:22]=[C:21]([C:18]2[N:14]3[CH2:15][CH2:16][CH2:17][C:12]([NH:5][C:4]4[CH:3]=[C:2]([F:1])[C:8]([F:9])=[C:7]([F:10])[CH:6]=4)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:13]3=[N:20][N:19]=2)[CH:26]=[CH:25][C:24]=1[C:27]1[O:31][C:30]([CH3:32])=[N:29][CH:28]=1

Participants

4

Reactant 2

HCID 27249913,4,5-TrifluoroanilineHCID 66604255Ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Product 1

HCID 66608898Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[(3,4,5-trifluorophenyl)amino]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateYield 56.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

To 3,4,5-trifluoroaniline (2.1 g) was added ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1 g) at room temperature, and the mixture was stirred at 100° C. overnight under a nitrogen atmosphere. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (719 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9abfafc842c641feaf12985c241cbcff
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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