Acetonitrile → HCID 67283319, compound

Participants

Reaction Steps

Ceric ammonium nitrate (201 mg, 2.6 eq) was added portionwise to a stirred solution of 5-(2-aminopyrimidin-5-yl)-7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (75 mg) in 9:1 acetonitrile:water (9 mL:1 mL). The reaction was stirred at room temperature overnight, and then another 200 mg of ceric ammonium nitrate was added. The reaction was stirred another 3 h, and then concentrated in vacuo. The crude was partitioned between EtOH and saturated potassium carbonate. The aqueous layer was re-extracted with ethanol 4×. The combined extracts were then dried over sodium sulfate, then concentrated and purified by chromatography (Gradient: 3:1 hexanes:EtOAc to EtOAc) yielding product (44 mg, 76% yield). 1HNMR (300 MHz, DMSO-d6) δ10.78 (s, 1H), 8.18 (s, 2H), 7.62 (d, 1H), 7.50-7.13 (m, 8H), 3.70 (m, 1H), 3.50-3.32 (m, 2H). HRMS (ES+) m/z calcd for C20H15Cl2N5O [M+H]+, 412.0732. found, 412.0726.

Provenance & Evidence