Sodium borohydride → HCID 15982019, compound

HRID 255260Notes

Reaction equation

HRID 255260 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-bb199891f99a44fe9639e0256e4c1391
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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