1H-imidazo[4,5-c]quinoline-1,2-diamine → [1,2,4]Triazolo[1',5':1,2]imidazo[4,5-c]quinoline

HRID 415504Notes

Reaction equation

HRID 415504 reaction equation
[N:1]1([NH2:15])[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:3]=[C:2]1[NH2:14].[N:16]1([NH2:30])[C:28]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:18]=[C:17]1[NH2:29]>>[CH:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[C:13]1[N:1]3[NH:15][CH:17]=[N:14][C:2]3=[N:3][C:4]=1[CH:5]=[N:6]2.[N:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[C:28]1[N:16]3[NH:30][CH:2]=[N:29][C:17]3=[N:18][C:19]=1[CH:20]=[N:21]2

Participants

4

Reactant 2

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

Product 2

HCID 66620118[1,2,4]Triazolo[1',5':1,2]imidazo[4,5-c]quinolineHCID 66620248[1,2,4]Triazolo[1',5':1,2]imidazo[4,5-c][1,5]naphthyridine

Procedure

In step (2) of Reaction Scheme VIII, 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 is treated with an ortho ester of Formula R2aC(O-alkyl)3 to provide a [1,2,4]triazolo[1′,5′:1,2]imidazo[4,5-c]quinoline or [1,2,4]triazolo[1′,5′:1,2]imidazo[4,5-c][1,5]naphthyridine of Formula LXVII. The reaction can be carried out by adding the ortho ester to a compound of Formula LXVI in a suitable solvent such as toluene. The reaction is carried out at a temperature high enough to drive off alcohol formed during the reaction; a Dean-Stark trap can be used to collect the volatiles.

Workup

  1. customIn step (2) of Reaction Scheme VIII

Sources & evidence

ORD record
ord-c1c724e585fd46e092056b3515f6ab0f
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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