Acetic Acid → HCID 58307450, compound

HRID 222799Notes

Reaction equation

HRID 222799 reaction equation
[CH:1]1([C@H:5]([NH:13][C:14]([C:16]2[C:21]([CH3:22])=[CH:20][C:19](=[O:23])[N:18]([NH2:24])[C:17]=2[CH3:25])=[O:15])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1.[CH:26](=O)[CH2:27][CH3:28].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:1]1([C@H:5]([NH:13][C:14]([C:16]2[C:21]([CH3:22])=[CH:20][C:19](=[O:23])[N:18]([NH:24][CH2:26][CH2:27][CH3:28])[C:17]=2[CH3:25])=[O:15])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 58307502HCID 58307502, compound

Product 1

HCID 58307450HCID 58307450, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-amino-2,4-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide (415 mg, 1.21 mmol), propionaldehyde (0.52 mL, 7.3 mmol) and acetic acid (0.5 mL, 9 mmol) in methanol (10 mL) was added sodium cyanoborohydride (0.27 g, 4.2 mmol) and the mixture was stirred under argon atmosphere for 3 days at room temperature. The crude reaction mixture was concentrated in vacuo, diluted with H2O (30 mL) and extracted with dichloromethane (3×30 mL). The combined organic phases were washed with brine, dried over MgSO4 and evaporated. The crude mixture was purified by flash chromatography, yield 34%. LC-MS (m/z) 386.5 (MH+); tR=1.63 (method C).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with H2O (30 mL)
  4. extractionextracted with dichloromethane (3×30 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe crude mixture was purified by flash chromatography, yield 34%

Sources & evidence

ORD record
ord-d04d803632494fb69a7ab3c300c08dc7
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Reaction notes

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