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

HRID 602254Notes

Reaction equation

HRID 602254 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 V, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XLIII is first reduced to a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XLIV, 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 XLV. Steps (2) and (3) 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-a1bb0fd2928c40bf914347a7ef0f7987
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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