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

HRID 549092Notes

Reaction equation

HRID 549092 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-f8d8e0eb790d48d6b84a56092d9a3b9d
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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