p-Toluenesulfonic acid monohydrate → N-(4-{4-amino-7-[(1E)-4-hydroxybut-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

Participants

Reaction Steps

A suspension of N-(4-{4-amino-7-[(1E)-4-(tetrahydro-2H-pyran-2-yloxy)but-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.05 g, 0.09 mmol) in methanol (3 mL) was treated with p-toluene sulfonic acid monohydrate (0.002 g, 0.0095 mmol). The reaction mixture was stirred for 15 hours at room temperature. Solvent was removed under reduced pressure. The crude material was purified by flash chromatography on silica gel using 10% methanol in dichloromethane to give 0.033 g (77%) of the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (s, 1H), 8.00–7.98 (m, 1H), 7.93 (s, 1H), 7.71–7.69 (m, 1H), 7.61–7.58 (m, 2H), 7.35–7.33 (m, 2H), 7.20 (m, 1H), 7.15–7.15 (m, 1H), 709–7.07 (m, 1H), 6.59–6.55 (m, 1H), 6.35–6.20 (m, 1H), 5.58 (brs, 2H), 4.65 (m, 1H), 4.04 (s, 3H), 3.91 (s, 3H), 3.57–3.54 (m, 2H), 2.42 (m, 2H); LCMS (conditions a) Rt 3.42 min (96%), M+ 499.3.

Provenance & Evidence