Succinic anhydride → (E)-3-[6-(2,5-Dioxo-pyrrolidin-1-yl)pyridin-3-yl]-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide

Participants

Reaction Steps

According to the procedure of Example 109, except substituting (E)-3-(6-amino-pyridin-3-yl)-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide (2.2 g, 6.6 mmol) for the (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide, and succinic anhydride (0.80 g, 8.0 mmol) in 1,4-dioxane (119 mL) was heated to reflux for 15 h overnight. The title compound (1.7 g, 61%) was prepared as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 8.78 (s, 1H), 8.01-7.91 (m, 1H), 7.80-7.72 (m, 2H), 7.70-7.63 (m, 1H), 7.43-7.39 (m, 3H), 7.01-6.92 (m, 1H), 5.01-4.85 (m, 2H), 3.21-3.10 (m, 3H), 2.90-2.85 (m, 4H), 2.44 (s, 3H); MS (ESI) m/e 420 (M+H)+

Provenance & Evidence