1,2-Dichloroethane → HCID 21084086, compound

Participants

Reaction Steps

To a stirred solution of the compound of Example 59 (174 mg, 0.5 mmol) in dry DCM (5 mL) was added allyl amine (29 mg, 0.5 mmol), triethylamine (101 mg, 1 mmol), and a catalytic amount of 4-dimethylaminopyridine followed by EDC (96 mg, 0.5 mmol). The reaction mixture was stirred at r.t. for 4 h and then poured into 2M HCl(aq) (20 mL). The product was extracted with DCM (2×20 mL) and the combined organic fractions dried (MgSO4), filtered and the solvent removed in vacuo. Purification by radial chromatography (silica, EtOAc) gave the title compound as a solid (70 mg). δH (CDCl3) 7.7–7.1 (11H, m), 4.48 (1H, d, J 10 Hz), 5.6–5.4 (1H, m), 5.28 (1H, bs), 4.84 (1H, dd, J 10, 1 Hz), 4.69 (1H, dd, J 10, 1 Hz), 3.8–3.6 (2H, m). LCMS (ES+) 387 (M+H)+.

Provenance & Evidence