Trifluoroacetic acid → 7-Methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid benzo[b]thiophen-2-ylmethyl-[(2S,3aS,7aS)-1-(octahydro-indol-2-yl)methyl]-amide

Participants

Reaction Steps

Experimental conditions analogous to Example 1, from 0.12 (0.31 mmol) of (2S,3aS,7aS)-2-{[(benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-octahydro-indole-1-carboxylic acid tert-butyl ester, 3 mL dichloromethane, 52 μL (0.37 mmol) of triethylamine, and 83 mg (0.34 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride and 0.4 mL trifluoroacetic acid. The compound was purified using reverse phase HPLC, mobile phase with a gradient 15-80% acetonitrile in 50 min, gave 104 mg of the product as the free base as an off-white solid. LC-MSD, m/z for C29H34N2O4S [M+H]+: 507.6. 1H NMR (400 MHz, CDCl3/HCl): δ 1.4-2.0 (m, 8 H), 1.7 (s, 6 H), 2.1-2.2 (m, 1 H), 2.4-2.5 (m, 1 H), 3.2 (bs, 1 H), 3.3-3.4 (m, 1 H), 3.7-3.8 (m, 1 H), 3.8 (s, 3 H), 4.2-4.4 (m, 2 H), 4.9-5.2 (m, 2 H), 6.8 (s, 1 H), 7.1 (s, 1 H), 7.3-7.4 (m, 2 H), 7.7-7.8 (m, 2 H), 7.9 (bs, 1 H), 11.6-11.8 (bs, 1 H).

Provenance & Evidence