3-Aminobenzamide → 4-(3-Carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide

Participants

Reaction Conditions

Reaction Steps

4-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide, (50 mg, 0.09 mmol), prepared as in reference 3, in glacial acetic acid (2 mL) is mixed with 3-aminobenzamide (24.5 mg, 0.18 mmol) and shaken at 80° C. for 24 hours. The resulting mixture is directly purified by preparative HPLC-MS to give 4-(3-carbamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide (42.9 mg, yield 73%); 1H NMR (400 MHz, DMSO-d6) δ 11.54 (s, 1H), 10.65 (s, 1H), 9.96 (s, 1H), 9.68 (s, 1H), 8.59 (d, J=13.1 Hz, 1H), 8.51 (s, 1H), 8.50 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 8.19 (d, J=10.1 Hz, 2H), 8.09 (d, J=7.9 Hz, 1H), 7.94 (s, 1H), 7.83 (d, J=3.9 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.57 (d, J=4.7 Hz, 1H), 7.43 (t, J=7.9 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J=8.5 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.43 (s, 3H), 2.34 (s, 3H); ESIMS m/z 654.1 (M++1).

Provenance & Evidence