N,N-Dimethylsulfamide → HCID 66844712, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10-cyclohexyl-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxylic acid (54 mg, 0.13 mmol) and N,N-dimethylsulfamide (81 mg, 0.65 mmol) in DMA (2 mL), was added DMAP (80 mg, 0.65 mmol), and EDCI-HCl (100 mg, 0.52 mmol). The reaction mixture was stirred at 60° C. for 2 h, cooled to rt, diluted with DMSO and MeOH and purified by prep HPLC (MeOH/H2O with 10 mM TFA buffer) to yield 10-cyclohexyl-N-((dimethylamino)sulfonyl)-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxamide (29 mg, 0.056 mmol, 43%) as a bright yellow solid. 1H NMR (500 MHz, CD3OD) δ 1.22-1.34 (m, 1H), 1.41-1.62 (m, 3H), 1.77-1.85 (m, 2H), 1.95-2.18 (m, 4H), 2.71 (s, 3H), 2.90-3.00 (m, 1H), 3.05 (s, 6H), 5.09 (d, J=15.9 Hz, 1H), 6.03 (d, =15.9 Hz, 1H), 7.67 (dd, J=8.2, 1.5 Hz, 1H), 7.79-7.87 (m, 4H), 8.00 (d, J=8.6 Hz, 1H), 8.33 (s, 1H). LCMS: m/e 519 (M+H)+, ret time 1.96 min.

Provenance & Evidence