Hydrochloric Acid → HCID 66745250, compound

Participants

Reaction Steps

Ethanesulfonyl chloride (43.25 mg, 31.87 μL, 0.3364 mmol) was added to a solution of tert-butyl 2-[3-(bis(tert-butoxycarbonyl)amino)-6-piperazin-1-yl-pyrazin-2-yl]indole-1-carboxylate (100 mg, 0.1682 mmol) and triethylamine (18.72 mg, 25.79 μL, 0.1850 mmol) in DCM (2 mL) at 0° C. and the reaction mixture allowed to stir at ambient temperature for 30 minutes. The reaction was then treated with HCl in dioxane (210.2 μL of 4 M, 0.8410 mmol) and allowed to stir at ambient temperature overnight. The mixture was concentrated in vacuo and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (5.5 mg, 8% Yield). 1H NMR (DMSO) d 1.25 (3H, t), 3.12 (2H, q), 3.30 masked signal, 3.59 (4H, m), 5.66 (2H, br s), 7.00-7.04 (1H, m), 7.14-7.18 (2H, m), 7.51 (1H, m), 7.58 (1H, m), 7.81 (1H, s), 11.25 (1H, br s) ppm; MS (ES+) 386.87

Provenance & Evidence