Triphenylphosphine → HCID 66604324, compound

Participants

Reaction Steps

Diethyl azodicarboxylate (0.012 mL, 0.074 mmol) was added to a solution of triphenylphosphine (19 mg, 0.074 mmol), 2-(3-chloro-4-hydroxyphenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (16 mg, 0.037 mmol) and 2-morpholinoethanol (9.0 μL, 0.074 mmol) in dry THF (0.5 mL) at RT under nitrogen. After stirring overnight, the solvent was removed and preparative HPLC (PHENOMENEX® Luna C18 30×100 10u Column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile, gradient of 10 to 100% B over 25 min at 30 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 2-(3-chloro-4-(2-morpholinoethoxy)phenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (4.9 mg, 8.2 nmol, 22% yield) as a solid. MS (ESI) m/z 536.38 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.26 (1H, s), 8.54 (1H, s), 8.34 (1H, d, J=2.01 Hz), 8.27 (1H, s), 8.21 (1H, dd, J=8.69, 2.14 Hz), 8.07 (1H, d, J=8.56 Hz), 7.84 (1H, s), 7.32 (1H, d, J=8.81 Hz), 7.20 (1H, d, J=2.01 Hz), 7.00 (1H, dd, J=8.81, 2.01 Hz), 4.26 (2H, t, J=5.79 Hz), 3.74-3.85 (4H, m), 3.53-3.66 (4H, m), 3.18-3.28 (4H, m), 2.78 (2H, t, J=5.67 Hz), 2.52-2.59 (4H, m).

Provenance & Evidence