3,4-Diaminoquinoline → HCID 178419901, compound

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Reaction Steps

In step (1) of Reaction Scheme X, a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XXIII is reacted with an acid chloride of Formula LXXVI to provide a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula LXXVII. The reaction can be carried out by adding an excess of the acid chloride to a solution of a compound of Formula XXIII in a suitable solvent such as dichloromethane or 1,2-dichloroethane in the presence of a tertiary amine such as triethylamine. The reaction can be carried out at ambient temperature or at a sub-ambient temperature. Acid chlorides of Formula LXXVI can be prepared from the corresponding alpha hydroxy acids using conventional methods. For example, (L)-lactic acid can be treated with acetyl chloride to provide O-acetyl-L-lactic acid. This material can then be treated with thionyl chloride to provide the acid chloride. See, Buisson, D. et al., Tetrahedron Assymetry, 10, pp 2997-3002 (1999).

Provenance & Evidence