Benzyloxy-3-nitro[1,5]naphthyridin-4-amine → Benzyloxyquinoline-3,4-diamine

HRID 221524Notes

Reaction equation

HRID 221524 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([N+:19]([O-])=O)=[C:17]([NH2:22])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:30][C:31]1[C:40]([N+:41]([O-])=O)=[C:39]([NH2:44])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][N:37]=2)[N:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:1]([O:8][C:9]1[C:18]([NH2:19])=[C:17]([NH2:22])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:30][C:31]1[C:40]([NH2:41])=[C:39]([NH2:44])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][N:37]=2)[N:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 66649873Benzyloxy-3-nitro[1,5]naphthyridin-4-amineHCID 66649911Benzyloxy-3-nitroquinolin-4-amine

Product 2

HCID 66958435Benzyloxyquinoline-3,4-diamineHCID 67157263Benzyloxy[1,5]naphthyridine-3,4-diamine

Procedure

In steps (6) and (7) of Reaction Scheme IV, the hydroxy group of a benzyloxy-3-nitroquinolin-4-amine or benzyloxy-3-nitro[1,5]naphthyridin-4-amine of Formula XL is protected to provide a compound of Formula XLI, which is reduced to provide a benzyloxyquinoline-3,4-diamine or benzyloxy[1,5]naphthyridine-3,4-diamine of Formula XLII. Steps (6) and (7) of Reaction Scheme IV can be carried out according to the methods described in steps (2) and (3) of Reaction Scheme I.

Workup

  1. customto provide a compound of Formula XLI, which

Sources & evidence

ORD record
ord-c508da0d5c514e48b3b10e3ac7038e63
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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