Acetic Acid → HCID 70872922, compound

HRID 1959178Notes

Reaction equation

HRID 1959178 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12](=[O:33])[C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:16]=[C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=2)[CH:14]=1.[CH3:34][NH:35][CH3:36].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12](=[O:33])[C:13]1[CH:18]=[C:17]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:16]=[C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:35]([CH3:36])[CH3:34])=[CH:27][CH:26]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 86672644HCID 86672644, compound

Product 1

HCID 70872922HCID 70872922, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-formylphenyl)-6-(piperidin-1-yl)isonicotinamide (0.2 g, 0.45 mmol) in methanol (12 mL), dimethyl amine (2.6 mL, 4.5 mmol, 2M solution in THF) and acetic acid (0.02 g, 0.45 mmol) were added and reaction mass stirred at rt for 90 min. Then reaction mass was cooled to 0° C. and sodium cyanoborohydride (0.056 g, 0.9 mmol) was added. Reaction stirred at 0° C. for 2 h and then stirred at rt for overnight. On completion, solvent was removed under reduced pressure, residue treated with water and extracted with ethyl acetate. Combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to afford crude material which was purified by column chromatography over silica gel obtaining N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-((dimethylamino)methyl)phenyl)-6-(piperidin-1-yl)isonicotinamide as light green solid (0.173 g, 79%).

Workup

  1. customreaction mass
  2. customThen reaction mass
  3. temperaturewas cooled to 0° C.
  4. customReaction
  5. stirringstirred at 0° C. for 2 h
  6. stirringstirred at rt for overnight
  7. customOn completion, solvent was removed under reduced pressure, residue
  8. additiontreated with water
  9. extractionextracted with ethyl acetate
  10. dry with materialCombined ethyl acetate layers were dried over sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customto afford crude material which
  13. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-99652db5095e4f1aa320b85c1ff8de3a
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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