Hydrochloric Acid → HCID 6480930, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(6-methoxypyridin-3-yl)-1H-indole-6-carboxylate (from Step 1, 1 eq.) was dissolved in a mixture THF:MeOH (0.07 M, 1:1, v/v) then an aqueous solution of LiOH monohydrate (3 eq, 0.21 M) was added. The reaction mixture was heated at 60° C. for 4 h. It was allowed to cool to RT, and then hydrochloric acid was added. The precipitate that formed was collected by filtration and dried in vacuo to give the title compound (90%). 1H NMR (400 MHz; DMSO-d6, 300 K) δ 1.17-1.28 (m, 3H), 1.65-1.86 (m, 7H), 2.45-2.55 (m, 1H), 2.8 (s, 3H), 2.96 (s, 3H), 3.94 (s, 3H), 4.91 (s, 2H), 6.97 (d, J 8.4, 1H), 7.62 (d, J 8.8, 1H), 7.65 (d, J 8.8, 1H), 7.82 (d, J 8.4, 1H), 7.95 (s, 1H), 8.11 (s, 1H), 12.6 (bs, 1H); MS (ES+) m/z 436 (M+H)+.

Provenance & Evidence