Triethylamine → HCID 68863999, compound

Participants

Reaction Steps

A mixture of Example 318E (50 mg, 0.14 mmol), triethylamine (0.1 mL, 0.71 mmol), acetonitrile (1 mL) and 1-(3-aminopropyl)-2-pipecoline (177 mg, 1.1 mmol) was purged with argon, sealed in a vial and microwaved at 150° C. for 55 minutes. Purification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min provided the desired product. MS (ESI(+)) m/e 490 (M+H)+; (ESI(−)) m/e 488 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.24 (br s, 1H), 9.71 (br s, 1H), 7.58 (dd, 1H), 7.42 (t, 1H), 7.13 (d, 1H), 6.87 (dd, 1H), 6.67 (m, 2H), 6.05 (m, 1H), 3.69 (s, 3H), 3.36 (m, 2H), 3.12 (m, 2H), 3.05 (m, 2H), 2.88 (m, 1H), 2.54 (q, 2H), 1.86 (m, 4H), 1.64 (m, 2H), 1.43 (m, 2H), 1.20 (d, 3H), 1.10 (t, 3H).

Provenance & Evidence