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 83077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83077
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

Komponenten

4

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-35f13e360d96448f9430109667183d79
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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