Indole → HCID 49820977, compound

Participants

Reaction Conditions

Reaction Steps

A solution of indole (0.117 g) in DMF (8 mL) was cooled to 0° C. then sodium hydride (0.06 g) was added. After 15 min, [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.395 g) was added. The reaction flask was sealed, heated at 150° C. for 1 h, cooled to room temperature, and diluted with water. The solid precipitate was collected by filtration then purified by chromatography (silica, 0 to 20% of a 49:1 MeOH:NH4OH mixture in dichloromethane) to furnish the title compound (0.156 g, 33%) as an off-white solid. MS m/e 477 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27-1.57 (m, 2H) 1.55-1.79 (m, 2H) 1.95-2.13 (m, 3H) 2.16 (s, 6H) 2.75-3.06 (m, 2H) 3.74-3.89 (m, 6H) 3.91-4.08 (m, 4H) 6.71 (d, J=3.39 Hz, 1H) 7.18 (s, 1H) 7.30 (s, 1H) 7.36 (s, 1H) 7.61 (s, 1H) 8.30 (d, J=3.77 Hz, 1H) 8.78 (d, J=7.91 Hz, 1H)

Provenance & Evidence