Acetyl chloride → HCID 178474044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-5-(3-amino-4-phenoxyphenyl)-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (120 mg, 0.241 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was cooled to 0° C. then treatd with acetyl chloride (25 mg, 0.3 mmol). The mixture was warmed to ambient temperature for one hour then the solvents were removed under reduced pressure and the residue purified by preparative RP-HPLC to give trans-N1-(5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxyphenyl)acetamide acetate (45 mg, 35%): 1H NMR (DMSO-d6, 400 MHz) δ 9.67 (bs, 1H), 8.11(s, 1H), 8.00(s, 1H), 7.40(t, 3H), 7.17(m, 2H), 7.05(d, 2H), 6.95(d, 1H), 6.30(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.14(s, 3H), 2.04(s, 3H), 1.8-2.0(m, 6H), 1.89(s, 3H), 1.44(m, 2H); MS MH+540.5; RP-HPLC (Hypersil HS, 5 μm, 1000 A, 4.6×250 mm; 5%-50% acetonitrile—0.05 M ammonium acetate over 25 min, 1 ml/min) tr 20.37 min.

Provenance & Evidence