O-propylhydroxylamine hydrochloride → HCID 52950749, compound

HRID 83055Notes

Reaction equation

HRID 83055 reaction equation
Cl.[NH2:2][O:3][CH2:4][CH2:5][CH3:6].[C:7]([CH:10]1[CH2:13][N:12]([C:14](=[O:28])/[CH:15]=[CH:16]/[C:17]2[CH:18]=[C:19]3[C:24](=[N:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)[CH2:11]1)(=O)[CH3:8]>CO.ClCCl>[O:28]=[C:14]([N:12]1[CH2:13][CH:10](/[C:7](=[N:2]\[O:3][CH2:4][CH2:5][CH3:6])/[CH3:8])[CH2:11]1)/[CH:15]=[CH:16]/[C:17]1[CH:18]=[C:19]2[C:24](=[N:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]2

Participants

4

Reactant 2

HCID 12283955O-propylhydroxylamine hydrochlorideHCID 67154676(E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 52950749HCID 52950749, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1-(Amino-oxy)-propane hydrochloride (32 mg, 0.29 mmol) was added to a solution of (E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (61.3 mg, 0.20 mmol) in a mixture methanol/dichloromethane (8:2, 3.5 mL) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol (95:5) as eluent. The title product was obtained as a white solid (56.0 mg, 76%).

Workup

  1. concentrationAfter concentration to dryness
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-25bfbaed23bb4609b724b4d93c031e2d
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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