4-Methylmorpholine → 4-{(2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-propenoyl}-2-piperazinone

Participants

Reaction Steps

A mixture of Example 11B (0.09 g, 0.23 mmol), 2-piperazinone (0.069 g, 0.69 mmol), HOBT (0.095 g, 0.7 mmol), N-methylmorpholine (0.22 mL, 0.92 mmol), and EDCI (0.136 g, 0.71 mmol) in DMF (1 mL) was stirred at room temperature overnight, treated with water (20 mL), and filtered. The filter cake was dried to provide 110 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 3.20–3.36 (br m, 2H), 3.71–3.91 (br m, 2H), 4.03–4.35 (m, 2H), 5.94 (br s, 2H), 6.92–7.15 (br m, 1H), 7.11–7.16 (m, 4H), 7.21 (t, J=7.3 Hz, 1H), 7.42–7.52 (m, 4H), 7.63 (s, 1H), 7.71 (d, J=14.9 Hz, 1H), 8.13 (br s, 1H), 8.33 (s, 1H); MS (ESI(−)) m/e 469.3 (M−H)−.

Provenance & Evidence