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

HRID 83077Notes

Reaction equation

HRID 83077 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]([CH:14]1[CH2:17][N:16]([C:18](=[O:38])/[CH:19]=[CH:20]/[C:21]2[CH:22]=[C:23]3[C:34](=[N:35][CH:36]=2)[NH:33][C:32](=[O:37])[C:25]2([CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)[CH2:24]3)[CH2:15]1)(=O)[CH3:12]>CO>[CH3:31][N:28]1[CH2:29][CH2:30][C:25]2([CH2:24][C:23]3[C:34](=[N:35][CH:36]=[C:21](/[CH:20]=[CH:19]/[C:18](=[O:38])[N:16]4[CH2:15][CH:14](/[C:11](=[N:10]/[O:9][CH2:2][C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=5)/[CH3:12])[CH2:17]4)[CH:22]=3)[NH:33][C:32]2=[O:37])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine 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 529508311'-methyl-6-[(E)-3-[3-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

O-benzylhydroxylamine hydrochloride (13.5 mg, 0.08 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 (23.0 mg, 0.06 mmol) in methanol (1.5 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 (9:1) as eluent. The title product was obtained as a pink solid (9 mg, 31%).

Workup

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

Sources & evidence

ORD record
ord-35f13e360d96448f9430109667183d79
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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