Binap, (A+-)- → 4-chloro-6-[3-(2-morpholin-4-yl-ethylamino)-benzylamino]-2H-phthalazin-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-aminomethyl-phenyl)-(2-morpholin-4-yl-ethyl)-amine hydrochloride (212 mg, 0.781 mmol), 6-bromo-4-chloro-2H-phthalazin-1-one (184 mg, 0.710), Pd2(dba)3 (65 mg, 0.071 mmol), rac-BINAP (142 mg, 0.228 mmol), NaOtBu (266 mg, 2.768 mmol) and DMA (5 mL) was heated to 85° C. until the reaction was completed by HPLC. The reaction was filtered through celite and purified by preparatory HPLC to yield 4-chloro-6-[3-(2-morpholin-4-yl-ethylamino)-benzylamino]-2H-phthalazin-1-one hydroformate (62 mg) as a light brown solid. 1H (400 MHz, d6-DMSO) δ: 2.29 (m, 4H), 2.36 (t, 2H), 3.02 (m, 2H), 3.48 (m, 4H), 4.24 (d, 2H), 5.38 (bs, 1H), 6.40 (dd, 1H), 6.47 (d, 1H), 6.51 (s, 1H), 6.77 (s, 1H), 6.97 (t, 1H), 7.07 (dd, 1H), 7.54 (t, 1H), 7.85 (d, 1H), 8.10 (s, 1H), 12.26 (s, 1H) ppm; m/z (M+1) 413.93.

Provenance & Evidence