O-propylhydroxylamine hydrochloride → 1'-methyl-6-[(E)-3-[3-[(E)-C-methyl-N-propoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one

HRID 83079Notes

Reaction equation

HRID 83079 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:34])/[CH:15]=[CH:16]/[C:17]2[CH:18]=[C:19]3[C:30](=[N:31][CH:32]=2)[NH:29][C:28](=[O:33])[C:21]2([CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH2:20]3)[CH2:11]1)(=O)[CH3:8]>CO.ClCCl>[CH3:27][N:24]1[CH2:25][CH2:26][C:21]2([CH2:20][C:19]3[C:30](=[N:31][CH:32]=[C:17](/[CH:16]=[CH:15]/[C:14](=[O:34])[N:12]4[CH2:11][CH:10](/[C:7](=[N:2]/[O:3][CH2:4][CH2:5][CH3:6])/[CH3:8])[CH2:13]4)[CH:18]=3)[NH:29][C:28]2=[O:33])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 12283955O-propylhydroxylamine hydrochlorideHCID 68338069(E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1'-methyl-1H-spiro[[1,8]naphthyridine-3,4'-piperidin]-2(4H)-one

Product 1

HCID 872895761'-methyl-6-[(E)-3-[3-[(E)-C-methyl-N-propoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1-(Aminooxy)propane hydrochloride (10.5 mg, 0.093 mmol) was added to a solution of (E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1′-methyl-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one (20.0 mg, 0.052 mmol) in methanol/dichloromethane (1.5 mL, 9:1) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using chloroforme/methanol (9:1) as eluent. Triturations in acetone allowed isolation of the title product as a white solid (9 mg, 39%).

Workup

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

Sources & evidence

ORD record
ord-d075ae3412924738953644a03d1a828b
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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