Sodium sulfate decahydrate → HCID 66604129, compound

HRID 71125Notes

Reaction equation

HRID 71125 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][C:6]1([C:29](=[O:31])[CH3:30])[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.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][C:6]1([CH:29]([OH:31])[CH3:30])[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

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 666040891-{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}ethanone

Product 1

HCID 66604129HCID 66604129, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 1-{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}ethanone (85.0 mg) in THF (1 mL) was added to a suspension of lithium aluminum hydride (13.5 mg) in THF (1 mL) under ice-cooling. The reaction mixture was stirred for 10 min under ice-cooling, and sodium sulfate decahydrate (140 mg) was added under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr and filtered, 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 (61.4 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. stirringThe reaction mixture was stirred at room temperature for 1 hr
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-06779e92b1c949c4a99c1c0f62a8bab2
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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