Hydrochloric Acid → HCID 15948896, compound

Participants

Reaction Steps

A solution of tert-butyl 13-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-5,6,7,8-tetrahydrothieno[2′,3′:4,5]pyrrolo[2,1-a][2,5]benzodiazocine-11-carboxylate (1 eq., prepared as described in Example 1, Step 5) in dry THF (0.14 M) was treated with borane-dimethylsulfide complex (20 eq., 2 M solution in THF) overnight at RT. A solution of HCl in methanol (40 eq., 1.25 M) was added to the reaction mixture, which was then heated to reflux for 1 h. All volatiles were evaporated in vacuo and the residual material was subjected to RP-HPLC purification (column: Waters XTERRA PREP MS C18, 10 μm; solvents: A: water+0.1% trifluoroacetic acid; B: MeCN+0.1% trifluoroacetic acid; 25% B in A isocratic for 3 min, linear to 20% A in B in 12 min) afforded the title compound after lyophilisation as a colourless powder (33%). 1H-NMR (500 MHz, DMSO-d6, 330 K, δ) 7.91 (s, 1H), 7.63 (d, J 7.1, 1H), 7.52-7.46 (m, 2H), 7.37 (d, J 6.3, 1H), 4.40 (dd, J 15.3, 4.9, 1H), 3.86 (d, J 13.9, 1H), 3.70-3.10 (m, 4H, hidden by the H2O signal), 3.05 (d, J 13.9, 1H), 3.04-2.84 (m, 2H), 2.84 (m, 6H), 2.69-2.60 (m, 1H) 2.55-2.50 (m, 1H, partially hidden by the DMSO signal), 2.02-1.09 (m, 10H). MS (ES+) m/z: 452 [M+H]+.

Provenance & Evidence