Diisopropylethylamine → 6-tert-butyl-N-(quinolin-4-ylmethyl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide

Participants

Reaction Steps

To a solution of 6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid (27 mg, 0.11 mmol), quinolin-4-yl-methanamine (15 mg, 0.09 mmol), and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (43 mg, 0.11 mmol) in DMF (0.4 mL) was added N,N-diisopropylethylamine (82 μL, 0.47 mmol). Tetrahydrofuran (0.8 mL) was added to dilute the solution. The reaction was left to stir overnight then concentrated and attempted purification by HPLC using 20-80% acetonitrile/water. Product isolated was less than 95% pure. It was purified again using 30-60% acetonitrile/water to obtain the product (23 mg, 64%) as a solid. m/z=376.8 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ 8.89-8.81 (m, 1H), 8.76-8.72 (m, 1H), 8.16-8.13 (m, 1H), 8.04-8.02 (m, 1H), 7.80-7.75 (m, 1H), 7.66-7.61 (m, 1H), 7.11 (t, 1H, J=4.63 Hz), 6.93-6.89 (m, 2H), 4.99-4.95 (m, 1H), 4.93-4.73 (m, 2H), 4.41-4.28 (m, 2H), 1.24 (d, 9H, J=1.94 Hz).

Provenance & Evidence