Water → HCID 178488851, compound

Participants

Reaction Steps

5-(3H-Imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenylamine (0.5 g, 2.1 mmol prepared as described above in Chemical Example 1) was dissolved in 15 mL pyridine at room temperature. Solid thiophene 2-sulfonyl chloride (0.38 g, 2.1 mmol) was added and the resulting blood red solution was stirred overnight The reaction mixture was poured into 250 mL water, stirred for 30 minutes, and filtered to give a pink solid. The solid was recrystallized from ethyl acetate after treatment with decolorizing charcoal to give 0.16 g of thiophene-2-sulfonic acid [5-(3H-imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenyl]-amide as an off-white solid; mp 252-254° C. 1H-NMR (DMSO-d6): δ 13.26 (d, 1H), 9.85 (bs, 1H), 8.27 (m, 2H), 8.02 (m, 2H), 7.87 (d, 1H), 7.43 (d, 1H), 7.16 (m, 3H), 3.59 (s, 3H) ppm. Anal. (C17H14N4O3S2) C,H,N values were within 0.4% of theoretical values.

Provenance & Evidence