Sodium borohydride → HCID 117667676, compound

HRID 712623Notes

Reaction equation

HRID 712623 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH:14]C(=O)C1C=CC=CC=1)=[O:13])[CH2:7][CH2:6][C:5]2=[O:23].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH:5]2[OH:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117667782HCID 117667782, compound

Product 1

HCID 117667676HCID 117667676, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the N-(6-bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-benzamide (188 mg, 0.50 mmol) in 2 mL of MeOH is added NaBH4 (38.0 mg, 1.00 mmol) in one portion. The mixture is stirred for 30 min. and concentrated to dryness. The residue is dissolved in 40 mL EtOAc/H2O, diluted with 10 mL EtOAc and quenched with 20 mL of saturated aqueous NH4Cl. The organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine, dried with MgSO4, filtered and concentrated. The crude material is applied to a silica preparative TLC plate and eluted with 100% EtOAc to give 81.5 mg of 6-bromo-4-hydroxy-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide. This is converted to the titled product using the procedure of Step 5 of Example 22.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is dissolved in 40 mL EtOAc/H2O
  3. additiondiluted with 10 mL EtOAc
  4. customquenched with 20 mL of saturated aqueous NH4Cl
  5. washThe organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluted with 100% EtOAc

Sources & evidence

ORD record
ord-80fee231599c4d07af25489d75292587
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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