3-(Trifluoromethyl)benzoyl chloride → HCID 11584925, compound

Participants

Reaction Steps

3-(5-Amino-2-methyl-phenyl)-1-[6-(3-dimethylamino-phenylamino)-pyrimidin-4-yl]-1-methyl-urea (0.26 mmol), 3-trifluoromethyl-benzoyl chloride (57 mg, 0.27 mmol) and DIEA (68 uL, 0.39 mmol) are dissolved in 10 mL anhydrous DMF. The reaction is stirred in the room temperature for 4 hours. After removing the solvent, the crude product is dissolved into DMSO and purified by reverse phase preparative HPLC to give the final product N-(3-{3-[6-(3-Dimethylamino-phenylamino)-pyrimidin-4-yl]-3-methyl-ureido}-4-methyl-phenyl)-3-trifluoromethyl-benzamide as the white solid; 1H NMR (600 MHz, DMSO-d6) δ 12.67 (s, 1H), 10.44 (s, 1H), 9.84 (s, 1H), 8.56 (s, 1H), 8.40 (d, J=11.8 Hz, 2H), 8.28 (s, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.94 (d, J=7.7 Hz, 1H), 7.76 (t, J=7.8 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.35 (t, J=8.1 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 6.81 (d, J=7.5 Hz, 1H), 6.64 (s, 1H), 6.59 (d, J=8.2 Hz, 1H), 3.35 (s, 3H), 2.92 (s, 6H), 2.35 (s, 3H); ESIMS m/z 565.3 (M++1).

Provenance & Evidence