N,N'-Dimethylethylenediamine → HCID 67298694, compound

Participants

Reaction Steps

A solution (0.1 M) of methyl 6-(2-fluorocyclohexyl)-5-(2-formylphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate and dimethylethylenediamine (1.5 eq.) in MeOH was stirred at RT for 3 h, then NaCNBH3 (excess) was added and the mixture was stirred for 3 days; evaporation to dryness gave a residue that was taken into EtOAc and washed with sat. NaHCO3-solution and brine, dried and concentrated i. vac. to obtain methyl 6-[2-(dimethylamino)ethyl]-13-[(1R,2S)-2-fluorocyclohexyl]-7-oxo-5,6,7,8-tetrahydrothieno[2′,3′:4,5]pyrrolo[2,1-a][2,5]benzodiazocine-11-carboxylate that was used without further purification. The latter was dissolved in dry THF (0.1M) and treated with 2M borane dimethylsulfide complex in THF (excess), and the mixture was stirred overnight at RT. 1.25M HCl in MeOH was added dropwise, the flask was opened and the mixture was stirred for 3 h at 85° C. Evaporation to dryness gave a residue that was hydrolised with 1M aq. KOH (3 eq.) in dioxane (85° C., 2 h); after quenching with 6M aq. HCl and removal of all volatiles the title compound was isolated by RP-HPLC. Yield: 60%. 1H-NMR (400 MHz, DMSO-d6, 300K, δ) 8.04 (d, 1H, J 2.2) 7.85-7.46 (m, 4H), 4.74-4.69 (m, 1H), 4.86-4.45 (m, 1H), 4.40 (bt, 1H, J 12.5), 3.74-3.42 (m, 8H), 2.88 (s, 3H), 2.87 (s, 3H), 2.74-2.61 (m, 1H), 2.26-1.03 (m, 8H); MS (ES+) m/z 470 (M+H)+.

Provenance & Evidence