Hydrochloric Acid → HCID 15947223, compound

Participants

Reaction Conditions

Reaction Steps

A solution (0.05 M) of methyl 12-cyclohexyl-5-[2-(dimethylamino)ethyl]-6,7-dihydro-5H-thieno[2′,3′:4,5]pyrrolo[1,2-d][1,4]benzodiazepine-10-carboxylate (from Step 1) in dioxane was treated with 1 N KOH solution (5 eq.). The mixture was stirred at 60° C. for 2 h then treated with 1 N hydrochloric acid. The solvents were removed in vacuo and the residue purified by RP-HPLC (column: Waters XTERRA PREP MS C18, 5 μm; solvents: A: water+0.1% trifluoroacetic acid; B: MeCN+0.1% trifluoroacetic acid; 10% B in A isocratic for 1 min, linear to 50% A in B in 4 min, linear to 40% A in B in 1 min, 40% A in B isocratic for 1 min, linear to 30% A in B in 1 min) to afford the title compound (59% over two steps) after lyophilisation as a solid. 1H-NMR (400 MHz DMSO-d6, 300K δ) 9.12 (bs, 1H), 7.93 (s, 1H), 7.48-7.23 (m, 4H), 4.18 (m, 2H), 3.46 (m, 4H), 3.13 (m, 2H), 2.67 (m, 1H), 1.78-1.27 (m, 10H). MS (ES+) m/z: 438 [M+H]+.

Provenance & Evidence