Hydrochloric Acid → HCID 67298900, compound

Participants

Reaction Steps

A solution (0.1 M) of methyl 12-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-6,7-dihydro-5H-thieno[2′,3′:4,5]pyrrolo[1,2-d][1,4]benzodiazepine-10-carboxylate (from Example 7, Step 5) in THF was treated with borane-dimethylsulfide complex (2 M solution in THF, 20 eq.). The mixture was stirred at RT for 2 h then treated with HCl in methanol (1.25 M) and heated at 75° C. for 30 mins. The solvents were removed in vacuo and the residue taken into EtOAc and washed with saturated NaHCO3 solution and brine, dried over sodium sulfate and concentrated in vacuo to give the title compound as a solid. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 7.99 (s, 1H), 7.40-7.36 (t, J 8, 1H), 7.29-7.27 (d, J 8, 1H), 7.23-7.21 (d, J 8, 1H), 7.14-7.10 (t, J 8, 1H), 4.17 (m, 2H), 3.82 (s, 3H), 3.43-3.39 (m, 2H), 3.20-3.17 (m, 2H), 2.70-2.67 (m, 1H), 2.32-2.23 (m, 2H), 2.01 (s, 6H), 1.81-1.23 (m, 10H). MS (ES+) m/z: 452 [M+H]+.

Provenance & Evidence