Acetic Anhydride → HCID 66604128, compound

HRID 71122Notes

Reaction equation

HRID 71122 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][C:6]1([CH2:29][OH:30])[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][C:24]([CH3:26])=[N:23][CH:22]=4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:13][N:14]=[C:7]12.[C:35](OC(=O)C)(=[O:37])[CH3:36].C(N(CC)CC)C.C1COCC1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:35]([O:30][CH2:29][C:6]1([CH2:5][C:4]2[CH:31]=[CH:32][C:33]([F:34])=[C:2]([F:1])[CH:3]=2)[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][C:24]([CH3:26])=[N:23][CH:22]=4)=[C:17]([O:27][CH3:28])[CH:16]=3)=[N:13][N:14]=[C:7]12)(=[O:37])[CH3:36]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66603794{8-(3,4-Difluorobenzyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methanol

Product 1

HCID 66604128HCID 66604128, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A catalytic amount of 4-dimethylaminopyridine was added to a mixture of {8-(3,4-difluorobenzyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methanol (80.0 mg), acetic anhydride (19.4 μL), triethylamine (28.6 μL) and THF (1 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and diluted with ethyl acetate, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (72.5 mg).

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water and saturated 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 (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6541e3ab76bb4257be7ca03c5b61e973
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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