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

HRID 1803364Notes

Reaction equation

HRID 1803364 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 V, a benzyloxy-3-nitroquinolin-4-amine or benzyloxy-3-nitro[1,5]naphthyridin-4-amine of Formula LVI is reduced to provide a benzyloxyquinoline-3,4-diamine or benzyloxy[1,5]naphthyridine-3,4-diamine of Formula LVII, which is then is treated with a halogen-substituted carboxylic acid equivalent to provide a benzyloxy-1H-imidazo[4,5-c]quinoline or benzyloxy-1H-imidazo[4,5-c][1,5]naphthyridine of Formula LVIII. Steps (6) and (7) of Reaction Scheme V can be carried out according to the methods described in steps (2) and (3) of Reaction Scheme I.

Sources & evidence

ORD record
ord-14dddab6a92e49f693c5ddcbccd3852a
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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