Sodium borohydride → HCID 86305666, compound

HRID 712600Notes

Reaction equation

HRID 712600 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[N:18][CH:19]=2)[N:16]([C:20]([NH2:22])=[O:21])[CH2:15][CH2:14][CH2:13]3)[CH:7]=[N:8][CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[N:18][CH:19]=2)[N:16]([C:20]([NH2:22])=[O:21])[CH2:15][CH2:14][CH2:13]3)[CH:7]=[N:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86305665HCID 86305665, compound

Product 1

HCID 86305666HCID 86305666, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(5-Acetyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (20 mg, 0.067 mmol) is dissolved in 2.0 mL of MeOH and NaBH4 (7.7 mg, 0.20 mmol) is added. The mixture is stirred for 30 min and then MeOH is removed at room temperature and saturated aqueous NH4Cl (2 mL) is added along with water (2 mL) and EtOAc (5 mL). The mixture is stirred for 5 min and the aqueous layer is separated and extracted with EtOAc (2×3 ml). The organic layers are combined and concentrated to give the crude product. Purification by reversed phase chromatography affords 15 mg of the titled product.

Workup

  1. customMeOH is removed at room temperature
  2. additionsaturated aqueous NH4Cl (2 mL) is added along with water (2 mL) and EtOAc (5 mL)
  3. stirringThe mixture is stirred for 5 min
  4. customthe aqueous layer is separated
  5. extractionextracted with EtOAc (2×3 ml)
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by reversed phase chromatography

Sources & evidence

ORD record
ord-d3f23a4dddad43d8a94caf2c61dcf914
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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