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

HRID 1663419Notes

Reaction equation

HRID 1663419 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 II, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XXIX is first reduced to a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XXX, which is then treated with a halogen-substituted carboxylic acid equivalent to provide a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XXXI. Steps (2) and (3) of Reaction Scheme II can be carried out according to the methods described in steps (2) and (3) of Reaction Scheme I.

Sources & evidence

ORD record
ord-179eb6e985ce4cfc9573a5d408e4acfd
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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