Benzenesulfonamide, 3-amino- → 4-(3-Sulfamoyl-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-aminobenzenesulfonamide (31 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-sulfamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide (35.3 mg, yield 57%); 1H NMR (400 MHz, DMSO-d6) δ 11.51 (s, 1H), 10.64 (s, 1H), 10.10 (s, 1H), 9.58 (s, 1H), 8.60 (s, 1H), 8.58 (s, 1H), 8.51 (s, 1H), 8.50 (s, 1H), 8.29 (s, 1H), 8.17 (d, J=8.1 Hz, 1H), 8.14 (s, 1H), 7.87 (d, J=3.9 Hz, 1H), 7.59 (d, J=1.8 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.53 (d, 5.9 Hz, 1H), 7.37 (s, 2H), 7.30 (d, J=8.5 Hz, 1H), 7.11 (d, J=3.9 Hz, 1H), 2.44 (s, 3H), 2.33 (s, 3H); ESIMS m/z 690.1 (M++1).

Provenance & Evidence