Diisopropylethylamine → HCID 68194764, compound

Participants

Reaction Steps

To a solution of Example 237A (100 mg, 0.214 mmol) in 5 mL N,N-dimethylformamide was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (61.5 mg, 0.321 mmol), 1-hydroxybenzotriazole hydrate (49.2 mg, 0.321 mmol), diisopropylethylamine (0.075 ml, 0.428 mmol) followed by N,N-dimethylpiperidin-4-amine (0.036 ml, 0.257 mmol). The reaction mixture was held at room temperature overnight, and then diluted with ethyl acetate. The organics were washed with aqueous saturated NaHCO3, water, and brine, then dried over MgSO4, filtered, and concentrated. The compound was triturated from the crude reaction mixture to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.21-1.55 (m, 2H) 1.63-1.98 (m, 2H) 2.13-2.43 (m, 6H) 2.73-3.12 (m, 2H) 7.14 (d, J=1.59 Hz, 1H) 7.48 (d, J=8.73 Hz, 2H) 7.58-7.81 (m, 4H) 7.86-8.02 (m, 3H) 9.06-9.33 (m, 1H) 11.04 (s, 1H). MS (ESI+) m/z 477.1 (M+H)+.

Provenance & Evidence