Acetic Acid → HCID 22319004, compound

HRID 547729Notes

Reaction equation

HRID 547729 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)C>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][CH2:27]2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 22318995HCID 22318995, compound

Product 1

HCID 22319004HCID 22319004, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

80 mg of 3-(2-cyanophenyl)-1-(piperidin-4-yl)methyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 2 ml of chloroform. To the mixture were added 73 mg of benzaldehyde, 97 mg of triacetoxy sodium borohydride and 41 mg of acetic acid, followed by stirring at room temperature for 4 hours. The reaction solution was diluted with chloroform, and washed with a saturated aqueous solution of sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate. Then the mixture was evaporated, and the residue was purified by NH silica gel chromatography (hexane/ethyl acetate system), to give 80 mg of the title compound.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThen the mixture was evaporated
  4. customthe residue was purified by NH silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-9f5493900fb44c8bb5d1c809fc43db43
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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