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

HRID 2105458Notes

Reaction equation

HRID 2105458 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[NH-:12].ClC1C2C(=CC=CC=2)[N:17]=[CH:16]C=1[NH-].NO>>[NH:17]1[C:2]2[C:11]3[N:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:16]1

Participants

4

Reactant 3

HCID 787HydroxylamineHCID 86625942HCID 86625942, compoundHCID 86625943HCID 86625943, compound

Product 1

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

Procedure

In step (1) of Reaction Scheme VII, an N-(4-chloro[1,5]naphthyridin-3-yl)amide or N-(4-chloroquinolin-3-yl)amide of Formula XXXII is reacted with a hydroxylamine of the Formula Boc-CH2—X—CH2—ONH2 and cyclized to provide a 1H-imidazo[4,5-c][1,5]naphthyridine or a 1H-imidazo[4,5-c]quinoline of Formula LX. The reaction can be carried out using the method described in step (3) of Reaction Scheme I. Hydroxylamines of the Formula Boc-CH2—X—CH2—ONH2 can be prepared by conventional methods.

Workup

  1. customIn step (1) of Reaction Scheme VII

Sources & evidence

ORD record
ord-b35a61f89b244ad58354c9f94795a88b
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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