Diisopropylethylamine → HCID 59837484, compound

Participants

Reaction Steps

O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (640 mg, 1.7 mmol) was added to a solution of 4-[4-(3-Morpholin-4-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carboxylic acid hydrochloride (500 mg, 1.3 mmol), methylamine hydrogen chloride (130 mg, 1.9 mmol) and Hunig's base (790 μL, 4.5 mmol) in N,N-dimethylformamide (5 mL). The mixture was stirred at room temperature for 2 hours and then concentrated in vacuo. The residue was partitioned between 2M NaOH solution (20 mL) and DCM (2×20 mL). The organics were combined, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1, by volume) to provide the title compound (355 mg, 76%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 1.93-2.00 (m, 2H), 2.01-2.08 (m, 2H), 2.37-2.40 (m, 2H), 2.48 (m, 4H), 2.50 (t, 2H), 2.70 (d, 3H), 3.67-3.80 (m, 8H), 4.02 (t, 2H), 6.88 (d, 2H), 7.22 (d, 2H). LRMS APCI+ m/z 363 [MH]+.

Provenance & Evidence