HCID 66620006, compound → HCID 178419901, compound

HRID 415497Notes

Reaction equation

HRID 415497 reaction equation
[N:1]1(O)[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]=[CH:2]1.[N:15]1(O)[C:27]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[CH:16]1>>[NH:1]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:3]=[CH:2]1.[NH:15]1[C:27]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[CH:16]1

Participants

4

Reactant 2

HCID 66620006HCID 66620006, compoundHCID 666208601H-imidazo[4,5-c]quinolin-1-ol

Product 2

HCID 178419901HCID 178419901, compoundHCID 1784207351h-Imidazo[4,5-c][1,5]naphthyridine

Procedure

In step (4) of Reaction Scheme I, a 1H-imidazo[4,5-c]quinolin-1-ol or 1H-imidazo[4,5-c][1,5]naphthyridin-1-ol of Formula XXIII is cyclized by an intramolecular displacement of the halogen under basic conditions to provide 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XXIV. The reaction can be carried out by adding a base such as potassium tert-butoxide or sodium hydride to a solution of a compound of Formula XXXIII in a suitable solvent such as tetrahydrofuran or N,N-dimethylformamide. The reaction can be carried out at ambient temperature. Alternatively, a solution of a compound of Formula XXXIII in a suitable solvent such as dichloromethane can be treated with an aqueous solution of a base such as potassium carbonate or sodium carbonate. The reaction can be carried out at ambient temperature.

Workup

  1. customIn step (4) of Reaction Scheme I

Sources & evidence

ORD record
ord-41c510579c30438d8cbab4fad33557be
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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