Hydrochloric Acid → HCID 68863569, compound

Participants

Reaction Steps

A solution of Example 149B (102 mg, 0.264 mmol) in dichloromethane (1.0 mL) was treated with 4-methylmorpholine (87 μL, 0.792 mmol), 4-dimethylaminopyridine (3 mg, 0.025 mmol), N,N,N′,-trimethyl-1,3-propanediamine (42.6 μL, 0.290 mmol), and bromotripyrrolidinophosphonium hexafluorophosphate (123.3 mg, 0.265 mmol), stirred at room temperature for 3 days, and treated with 1N HCl. The aqueous layer was extracted with ethyl acetate three times and the combined organic phases were washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 484 (M+H)+; (ESI(−)) m/e 482 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.49 (s, 1H), 9.26 (s, 1H), 8.02 (d, 1H), 7.94 (dd, 1H), 7.1 (dd, 1H), 7.72 (dt, 1H), 7.61-7.48 (m, 5H), 3.84 (s, 3H), 3.19 (br s, 2H), 3.07 (m, 2H), 2.82 (d, 6H), 2.67 (s, 3H), 1.98 (quint, 2H).

Provenance & Evidence