Triethyl orthoacetate → HCID 178432311, compound

HRID 602257Notes

Reaction equation

HRID 602257 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:27]=1N)=NC=CC=2)([O-])=O.N1C2C(=CC=CC=2)C(N)=[C:31](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.C(OCC)(OCC)(OCC)C>>[CH3:18][C:27]1[NH:14][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]=1.[CH3:30][C:31]1[NH:51][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]=1

Participants

7

Reactant 5

HCID 66221Triethyl orthoacetateHCID 2800053-Nitroquinolin-4-amineHCID 15142893,4-DiaminoquinolineHCID 131227883-Nitro-1,5-naphthyridin-4-amineHCID 22172703[1,5]Naphthyridine-3,4-diamine

Product 2

HCID 178432311HCID 178432311, compoundHCID 178432312HCID 178432312, compound

Procedure

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

Sources & evidence

ORD record
ord-0741b8f7ea3d431a8755f66e6d031645
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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