3-Aminobenzamide → HCID 11284996, 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-aminobenzamide (34 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 and concentrated. The residue is purified by preparative HPLC-MS to give 4-(3-carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-benzoylamino]-phenyl}-amide (18.5 mg, yield, 60%); 1H NMR (400 MHz, DMSO-d6) δ 11.52 (s, 1H), 10.31 (s, 1H), 9.99 (s, 1H), 8.60 (s, 1H), 8.52 (d, J=1.71 Hz, 1H), 8.23 (s, 1H), 8.12 (d, J=7.59 Hz, 1H), 8.00 (s, 1H), 7.98 (d, J=8.02 Hz, 2H), 7.87 (d, J=3.89 Hz, 1H), 7.59 (dd, J=17.87, 9.00 Hz, 2H), 7.49 (d, J=7.98 Hz, 2H), 7.47 (s, 1H), 7.38 (s, 1H), 7.29 (d, J=8.48 Hz, 1H), 7.11 (d, J=3.89 Hz, 1H), 3.75 (s, 2H), 3.43-2.79 (m, 8H), 2.50 (s, 3H), 2.49 (s, 3H); ESIMS m/z 618.20 (M++1).

Provenance & Evidence