3-Nitroquinolin-4-amine → HCID 178419901, compound

HRID 602255Notes

Reaction equation

HRID 602255 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[N+]([C:18]1C=NC2C(C=1N)=NC=CC=2)([O-])=O.N1C2C(=CC=CC=2)C(N)=C(N)[CH:30]=1.[N:41]1[C:50]2[C:45](=[N:46][CH:47]=[CH:48][CH:49]=2)[C:44]([NH2:51])=[C:43]([NH2:52])[CH:42]=1>>[NH:14]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[CH:18]1.[NH:51]1[C:44]2[C:45]3[N:46]=[CH:47][CH:48]=[CH:49][C:50]=3[N:41]=[CH:42][C:43]=2[N:52]=[CH:30]1

Participants

6

Reactant 4

HCID 2800053-Nitroquinolin-4-amineHCID 15142893,4-DiaminoquinolineHCID 131227883-Nitro-1,5-naphthyridin-4-amineHCID 22172703[1,5]Naphthyridine-3,4-diamine

Product 2

HCID 178419901HCID 178419901, compoundHCID 1784207351h-Imidazo[4,5-c][1,5]naphthyridine

Procedure

In steps (2) and (3) of Reaction Scheme VI, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula LII is first reduced to a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula LIII, which is then treated with a carboxylic acid equivalent to provide a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula LIV. Steps (2) and (3) of Reaction Scheme VI can be carried out according to the methods described in steps (2) and (3) of Reaction Scheme I.

Sources & evidence

ORD record
ord-26428a8592e74c2d8073a0193a15d76d
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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