Benzenesulfonyl chloride → HCID 58869098, compound

Participants

Reaction Conditions

Reaction Steps

A modified version of the general methods described in Parts D-G of Example 6 was sequentially followed with 5-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-pentan-2-one (5.27 g, 17.8 mmol) used in lieu of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde as the starting substrate. The formation of the O-methyl oxime, analogous to Part D of Example 6, was performed in the absence of sodium hydroxide and the pH of the reaction mixture was adjusted to ˜8 after completion of the reaction. The reduction of the oxime, analogous to Part E of Example 6, was complete after running overnight. Prior to addition of the ammonium hydroxide in the step analogous to Part G of Example 6, the reaction mixture was cooled to 0° C. and para-toluenesulfonyl chloride (1.1 eq) was substituted for phenylsulfonyl chloride. The reaction was incomplete after an hour, and additional para-toluenesulfonyl chloride (0.5 eq) was added. After the final step in the sequence, purification by HPFC (0-30% CMA in chloroform), trituration from acetonitrile, filtration, and drying of the material in a vacuum oven at 80° C. afforded 77 mg of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)1-methyl-butyl]-N-methoxyacetamide as an off-white powder, mp 158-159° C. Anal. calcd for C20H28N6O2: C, 62.48; H, 7.34; N, 21.86. Found: C, 62.19; H, 7.61; N, 22.09.

Provenance & Evidence