1,2-Dichloroethane → HCID 25064115, compound

Participants

Reaction Steps

To a stirred solution of Example 28 (0.35 g, 0.99 mmol) in DCM (10 mL) were added 1-hydroxybenzotriazole hydrate (0.015 g, 0.11 mmol), DIPEA (0.175 mL, 1.00 mmol) and EDC (210 mg, 1.08 mmol). The reaction mixture was stirred at r.t. for 5 minutes. Methylamine (0.185 mL, 33% wt. solution in EtOH, 1.97 mmol) was added and stirring was continued at r.t. for 20 h. The reaction mixture was then diluted with DCM (100 mL) and then washed with sat. aqueous NaHCO3 solution (100 mL), then water (100 mL) and brine (100 mL). The organic fraction was dried (NaSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0-10% MeOH/DCM) gave the title compound (0.22 g, 61%) as a white solid. δH (DMSO-d6) 8.07 (1H, d, J 8.5 Hz), 7.83-7.75 (1H, m), 7.19-7.12 (2H, m), 4.34-4.27 (2H, m), 4.04-3.97 (2H, m), 2.70 (3H, d, J 4.5 Hz), 2.47 (3H, s). LCMS (ES+) 368.1 and 370.1 (M+H)+, RT 3.50 minutes (Method 7).

Provenance & Evidence