2-Methoxyaniline → HCID 11754871, compound

Participants

Reaction Conditions

Reaction Steps

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (30 mg) was dissolved in o-anisidine (0.75 ml) and heated in a microwave oven (180° C., 20 min). The resulting mixture was diluted with acetonitrile (1 ml) and acetic acid (0.5 ml) and subjected to semi-preparative HPLC-C18. The fractions containing product (it co-elutes with o-anisidine) were pooled and evaporated in vacuo. The residue was dissolved in EtOAc (20 ml) and washed with 1% aqueous NaHCO3 (10 ml). The organic phase was treated with activated carbon and MgSO4, filtered and evaporated in vacuo. The oily residue was triturated with n-heptane (1 ml) and a few drops of EtOAc, which caused the product to crystallize. It was collected by filtration and washed with EtOAc to give the pure product as a white powder (10 mg, 27%). A second crop (2.9 mg) crystallized from the combined mother liquor and washing liquids.

Provenance & Evidence