Water → HCID 66603957, compound

HRID 71165Notes

Reaction equation

HRID 71165 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:5][O:6][C:7]1([C:30]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:31])[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:26][C:25]([CH3:27])=[N:24][CH:23]=4)=[C:18]([O:28][CH3:29])[CH:17]=3)=[N:14][N:15]=[C:8]12.[C:42](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:5][O:6][C:7]1([C:30]([N:32]([CH3:42])[CH2:33][C:34]([F:37])([F:35])[F:36])=[O:31])[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:26][C:25]([CH3:27])=[N:24][CH:23]=4)=[C:18]([O:28][CH3:29])[CH:17]=3)=[N:14][N:15]=[C:8]12

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 666082508-[(3,4-difluorobenzyl)oxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-N-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide

Product 1

HCID 66603957HCID 66603957, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-[(3,4-difluorobenzyl)oxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-N-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide (200 mg) in DMF (5 mL) were added cesium carbonate (169 mg) and methyl iodide (0.026 mL) at room temperature. After stirring at room temperature for 2 hr, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate/THF (2/1). The extract was washed with 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) to give the title compound (75 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate/THF (2/1)
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4eff8609f4a748bd8ca5c49effe41b64
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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