O-ethylhydroxylamine hydrochloride → 6-[(E)-3-[3-[(Z)-N-ethoxy-C-methylcarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1H-1,8-naphthyridin-2-one

HRID 634011Notes

Reaction equation

HRID 634011 reaction equation
Cl.[NH2:2][O:3][CH2:4][CH3:5].[C:6]([CH:9]1[CH2:12][N:11]([C:13](=[O:27])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[C:18]3[C:23](=[N:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]3)[CH2:10]1)(=O)[CH3:7]>CO.ClCCl>[CH2:4]([O:3]/[N:2]=[C:6](\[CH:9]1[CH2:12][N:11]([C:13](=[O:27])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[C:18]3[C:23](=[N:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]3)[CH2:10]1)/[CH3:7])[CH3:5]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine 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 529507516-[(E)-3-[3-[(Z)-N-ethoxy-C-methylcarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]-3,4-dihydro-1H-1,8-naphthyridin-2-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1-(Aminooxy)ethane hydrochloride (23 mg, 0.23 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 (50.0 mg, 0.16 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 ethyl acetate/methanol (95:5) as eluent. The title product was obtained as a white solid (20 mg, 35%).

Workup

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

Sources & evidence

ORD record
ord-b5e17ede2cb9440e8dea0df22394a65c
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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