Benzoyl chloride → HCID 178480935, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-5-[4-(aminomethyl)phenyl]-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.119 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was cooled to 0° C. then treated with benzoyl chloride (19 mg, 0.13 mmol). The mixture was allowed to warm to ambient temperature and stirred for 1 hour. The solvents were removed under reduced pressure then the residue was purified by preparative reverse phase chromatography to give trans-N1-(4-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}benzyl)benzamide (50 mg) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 9.08(t, 1H), 8.13(s, 1H), 7.91(m, 2H), 7.4-7.54(m, 8H), 6.0(bs, 2H), 4.53(m, 3H), 2.30-2.40(m, 5H), 2.15(s, 3H), 1.85-1.89(m, 10H), 1.43-1.46 (m, 2H); RP-HPLC (Hypersil HS C18, 5μm, 100 A, 250×4.6 mm; 5%-50% acetonitrile over 25 min, 1 mL/min) tr 18.20 min.; MS:MH+ 524.3.

Provenance & Evidence