p-Toluenesulfonic acid → HCID 46841133, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-amino-N-(4-morpholinophenyl)benzamide (1.71 g, 5.75 mmol) in DMA (20 mL) was added 4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylbenzaldehyde (1.77 g, 5.75 mmol), NaHSO3 (0.66 g, 6.33 mmol), and p-TsOH (0.22 g, 1.15 mmol). The reaction mixture was heated at 120° C. overnight, then heated to 140° C., and additional sodium bisulfite (2.60 g, 25 mmol) was added. After an additional 17 hours, the reaction mixture was cooled and diluted with 5% lithium chloride solution (120 mL), extracted with ethyl acetate (200 mL), and then washed with water (2×100 mL) and then brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was triturated with 1:1 hexanes/methylene chloride. Purification by flash chromatography on silica gel, eluting with 30% ethyl acetate/hexanes to 70% ethyl acetate/hexanes, afforded the title compound as a white solid (0.223 g, 8%). 1H-NMR (500 MHz, DMSO-d6) δ 8.16 (dd, J=7.98, 1.3 Hz, 1H), 7.87 (td, J=8.4, 1.5 Hz, 1H), 7.72 (d, J=7.9 Hz, 1H), 7.57 (td, J=8.1, 1.1 Hz, 1H), 7.11 (d, J=8.9 Hz, 2H), 7.03 (s, 2H), 6.86 (d, J=9.0 Hz, 2H), 4.82 (br s, 1H), 3.68-3.72 (m, 6H), 3.63-3.67 (m, 2H), 3.08-3.09 (m, 4H), 2.10 (s, 6H).

Provenance & Evidence