Ammonia → HCID 66604492, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-chloro-4-(2-chloroethoxy)phenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (20 mg, 0.041 mmol), potassium iodide (14 mg, 0.082 mmol), K2CO3 (11 mg, 0.082 mmol) and homomorpholine hydrochloride (23 mg, 0.17 mmol) in DMSO (0.2 mL) in a vial was heated at 70° C. for 40 hrs. 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 20 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 2-(4-(2-(1,4-oxazepan-4-yl)ethoxy)-3-chlorophenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (16 mg, 0.029 mmol, 71% yield) as a yellow solid. MS (ESI) m/z 550.24 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.22 (1H, d, J=8.85 Hz), 8.16 (1H, d, J=2.14 Hz), 8.06 (1H, s), 7.99 (1H, dd, J=8.55, 2.44 Hz), 7.19 (1H, d, J=8.85 Hz), 7.10 (1H, d, J=2.14 Hz), 7.03 (1H, dd, J=8.85, 2.14 Hz), 4.27 (2H, t, J=5.34 Hz), 3.86-3.94 (4H, m), 3.76-3.85 (4H, m), 3.27-3.31 (4H, m), 3.10 (2H, t, J=5.34 Hz), 2.94-3.02 (4H, m), 1.97 (2H, m).

Provenance & Evidence