Ammonia → HCID 66604332, compound

Participants

Reaction Steps

A suspension of 2-(5-formylfuran-2-yl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (14 mg, 0.022 mmol), morpholine (19 uL, 0.22 mmol), and sodium triacetoxyborohydride (24 mg, 0.11 mmol) in 1,2-dichloroethane (0.3 mL) was stirred at RT overnight. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA; gradient of 0 to 60% B over 10 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH gave 7-morpholino-2-(5-(morpholinomethyl)furan-2-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (7.8 mg, 0.016 mmol, 44% yield). MS (ESI) m/z 462.33 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.27 (1H, d, J=8.55 Hz), 7.98 (1H, s), 7.11 (1H, d, J=3.05 Hz), 6.98 (1H, dd, J=8.70, 1.98 Hz), 6.91 (1H, d, J=1.83 Hz), 6.42 (1H, d, J=3.36 Hz), 3.88-3.98 (4H, m), 3.75-3.84 (4H, m), 3.65 (2H, s), 3.29-3.38 (4H, m), 2.53-2.69 (4H, m).

Provenance & Evidence