Sodium borohydride → HCID 15982019, compound

HRID 1644379Notes

Reaction equation

HRID 1644379 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([NH:22][CH2:23][C:24]4[CH:25]=[CH:26][C:27]5[O:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=5[N:33]=4)[CH2:18][CH2:17]3)[C:8]=2[CH:35]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([NH:22][CH2:23][C:24]4[CH:25]=[CH:26][C:27]5[O:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=5[N:33]=4)[CH2:18][CH2:17]3)[C:8]=2[CH:35]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15981895HCID 15981895, compound

Product 1

HCID 15982019HCID 15982019, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[({1-[2-(6-Acetyl-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Example 45) (309 mg, 0.645 mmol) was reduced with sodium borohydride (47 mg, 2 equivalents) in methanol (12 mL) at 0° C. After quenching the reaction with water, the reaction mixture was concentrated under reduced pressure and extracted with chloroform. The chloroform layer was washed with brine and dried over magnesium sulfate and concentrated to dryness to give the as an off-white solid, 202 mg (95%).

Workup

  1. customAfter quenching
  2. customthe reaction with water
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customto give the as an off-white solid, 202 mg (95%)

Sources & evidence

ORD record
ord-08755f304c1f4ed6add359102ffb866a
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

Loading…