Sodium borohydride → HCID 86691836, compound

HRID 1616224Notes

Reaction equation

HRID 1616224 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:26])=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH3:25])[C:17](=[O:24])[N:18]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]3=[CH:12][CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[CH3:22][C:20]([CH3:21])([CH3:23])[CH2:19][N:18]1[C:13]2[C:14](=[N:15][C:10]([C:8]3[CH:9]=[C:4]([C@@H:1]([OH:3])[CH3:2])[CH:5]=[CH:6][C:7]=3[CH3:26])=[CH:11][CH:12]=2)[N:16]([CH3:25])[C:17]1=[O:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86691837HCID 86691837, compound

Product 1

HCID 86691836HCID 86691836, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a microwave vial was added 5-(5-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (15-7) (15 mg, 0.043 mmol) and sodium borohydride (2.5 mg, 0.064 mmol) under nitrogen. The mixture was dissolve in methanol (0.4 ml), and allowed to stir at room temperature for 1 hour. The reaction was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 1-(2,2-dimethylpropyl)-5-{5-[(1S)-1-hydroxyethyl]-2-methylphenyl}-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (25-1). HRMS (M+H)+: observed=354.2178, calculated=354.2176.

Workup

  1. custompassed through a syringe
  2. filtrationfilter
  3. customThe solution was purified
  4. customthe desired fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9db0416204f643b5afa3dac831dccd87
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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