Cyanogen Bromide → 1H-imidazo[4,5-c]quinoline-1,2-diamine

HRID 415503Notes

Reaction equation

HRID 415503 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13]C(OC(C)(C)C)=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:21][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:31]=1[NH:32][NH:33]C(OC(C)(C)C)=O)=[N:29][CH:28]=[CH:27][CH:26]=2.[N:41]#[C:42]Br>>[N:12]1([NH2:13])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:22]1[NH2:21].[N:32]1([NH2:33])[C:31]2[C:30]3[N:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:21]=[C:42]1[NH2:41]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylateHCID 57931084Tert-butyl 2-(3-amino[1,5]naphthyridin-4-yl)hydrazinecarboxylate

Product 2

HCID 578537771H-imidazo[4,5-c]quinoline-1,2-diamineHCID 666198741H-imidazo[4,5-c][1,5]naphthyridine-1,2-diamine

Procedure

In step (1) of Reaction Scheme VIII, a tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate or a tert-butyl N′-(3-amino[1,5]naphthyridin-4-yl)hydrazinecarboxylate of Formula XXXIX is reacted with cyanogen bromide to provide a 1H-imidazo[4,5-c]quinoline-1,2-diamine or 1H-imidazo[4,5-c][1,5]naphthyridine-1,2-diamine of Formula LXVI. The reaction can be carried out by adding cyanogen bromide to a solution of compound of Formula XXXIX in a suitable solvent such as ethanol and heating.

Workup

  1. customIn step (1) of Reaction Scheme VIII

Sources & evidence

ORD record
ord-2d9c2cbc33d04fe691428b2a89c02238
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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