4-Methylmorpholine → HCID 68864053, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 149B (228 mg, 0.592 mmol) in dimethylformamide (3.0 mL) was treated with 4-methylmorpholine (230 μL, 2.07 mmol), cooled to 0° C., treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (450 mg, 1.18 mmol), stirred for 1 hour, treated with 3-(N,N-diethylamino)propylamine (166 μL, 1.18 mmol), warmed to room temperature, stirred overnight, treated with distilled water, and extracted with ethyl acetate three times. The combined extracts 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 9.36 (s, 1H), 9.21 (br s, 1H), 9.11 (t, 1H), 8.04 (d, 1H), 7.94 (dd, 1H), 7.79-7.68 (m, 4H), 7.62 (d, 1H), 7.60-7.53 (m, 3H), 3.81 (s, 3H), 3.67 (m, 2H), 3.26 (m, 6H), 1.26 (t, 6H).

Provenance & Evidence