Benzyloxyamine hydrochloride → 1h-Imidazo[4,5-c][1,5]naphthyridine

HRID 415496Notes

Reaction equation

HRID 415496 reaction equation
ClC1C2C(=CC=CC=2)[N:5]=[CH:4]C=1[NH-].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]=[CH:16][C:15]=1[NH-:24].Cl.C(ON)C1C=CC=CC=1>>[NH:5]1[C:14]2[C:23]3[N:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=[CH:4]1

Participants

4

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 86625942HCID 86625942, compoundHCID 86625943HCID 86625943, compound

Product 1

HCID 1784207351h-Imidazo[4,5-c][1,5]naphthyridine

Procedure

In step (2) of Reaction Scheme I, an N-(4-chloroquinolin-3-yl)amide or N-(4-chloro[1,5]naphthyridin-3-yl)amide of Formula XXI is reacted with O-benzylhydroxylamine hydrochloride to provide a benzyloxy substituted 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XXII. The reaction can be carried out by combining a compound of Formula XXI and O-benzylhydroxylamine hydrochloride in an alcoholic solvent, such as isopropanol, and heating the resulting mixture.

Workup

  1. customIn step (2) of Reaction Scheme I

Sources & evidence

ORD record
ord-3c2803924b944c9ea5dc5a9fdaf3d8ac
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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