2,3-Diaminopyridine → HCID 59243043, compound

Participants

Reaction Steps

The subsequent steps have been described previously and include formation of the amide (LC/MS calculated and found 383) from the 3-(2-fluorobenzyloxy)-5-nitrobenzoic acid and 2,3-diaminopyridine with HBTU, TEA, and DMF followed by cyclization to the imidazopyridine (LC/MS calculated and found 365) in the microwave at 180° C. in 1:1 BuOH-glacial acetic acid for 30 min. Finally, the nitro group was reduced to the amine using tin (II) chloride in refluxing ethyl alcohol (LC/MS calculated and found 335) and the resulting amine was reacted with 2-thiophene sulfonyl chloride to form the sulfonamide final product (LC/MS calculated and found 481). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.45 (m, 1H), 7.84 (m, 1H), 7.70 (m, 2H), 7.59 (m, 3H), 7.5-7.2 (m, 5H), 7.06 (m, 1H), 6.99 (m, 1H), 6.71 (m, 1H), 5.16 (s, 2H); Calc'd for C23H17FN4O3S2; m/z (M+H+)=481; found 481.

Provenance & Evidence