p-Toluenesulfonic acid → HCID 49820827, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vessel was charged with [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.2 g), indoline (0.12 g), p-toluenesulfonic acid (0.01 g), and DMF (3 mL). The vessel was sealed and heated at 150° C. under microwave irradiation for 4 h. The reaction mixture was cooled to room temperature and the solid precipitate was filtered and purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane) to furnish the title compound (0.09 g, 38%) as an off-white solid. MS m/e 479 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36-1.65 (m, 2H) 1.85 (d, J=11.30 Hz, 2H) 2.06 (t, J=10.74 Hz, 2H) 2.44 (br. s., 6H) 2.97 (d, J=11.30 Hz, 2H) 3.12 (t, J=8.48 Hz, 3H) 3.67-3.93 (m, 10H) 4.17 (t, J=8.67 Hz, 2H) 6.84 (t, J=7.35 Hz, 1H) 7.03-7.29 (m, 3H) 8.31 (d, J=7.91 Hz, 1H).

Provenance & Evidence