Acetyl chloride → HCID 11296729, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-benzoylamino]-phenyl}-amide resin (50 mg, 0.05 mmol), prepared as in reference 2, in n-butanol (2 mL) is mixed with acetyl chloride (17.8 μL, 0.25 mmol) and 3-aminobenzenesulfonamide (43 mg, 0.25 mmol), and shaken at 80° C. for 24 hours. The resulting mixture is filtered and the resin is treated with TFA/CH2Cl2/H2O (45/50/5) (600 μL) for 30 minutes before filtering and washing with CH2Cl2 (3×2 mL), MeOH (3×2 mL). The washes are then combined together with n-butanol and concentrated. The residue is purified by preparative HPLC-MS to give 4-(3-sulfamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-benzoylamino]-phenyl}-amide (18.0 mg, yield 55%); 1H NMR (400 MHz, DMSO-d6) δ 11.45 (s, 1H), 10.27 (s, 1H), 10.09 (s, 1H), 8.59 (s, 1H), 8.49 (s, 1H), 8.29 (s, 1H), 8.17 (d, J=7.95 Hz, 1H), 7.95 (d, J=7.94, 2H), 7.87 (d, J=3.85 Hz, 1H), 7.54 (dd, J=7.61, 15.51 Hz, 2H), 7.52 (s, 1H), 7.45 (d, J=7.88 Hz, 2H), 7.37 (s, 2H), 7.25 (d, J=8.30 Hz, 1H), 7.11 (d, J=3.88 Hz, 1H), 3.69 (s, 2H), 3.54-3.3.17 (m, 2H), 3.01-2.93 (m, 6H), 2.75 (s, 3H), 2.41 (s, 3H); ESIMS m/z 654.20 (M++1).

Provenance & Evidence