Ammonia → HCID 66605029, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of crude methyl 2-(4-chlorophenyl)-7-(3-morpholinopropoxy)-5H-pyrido[3,2-b]indole-4-carboxylate (75 mg, 0.16 mmol) in 7 N NH3 in MeOH (4 mL) in a sealed microwave vial was heated at 80° C. overnight. The product was isolated by preparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=30:70 to A:B=0:100 [A=10 mM NH4OAc in 5% aq. CH3CN; B=10 mM NH4OAc in 95% aq. CH3CN] over 20 min) followed by removal of the solvents on the SPEEDVAC® to leave 2-(4-chlorophenyl)-7-(3-morpholinopropoxy)-5H-pyrido[3,2-b]indole-4-carboxamide (34.6 mg, 0.071 mmol, 45% yield) as a yellow solid. MS (ESI) m/z 465.0 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.45 (1H, s), 8.57 (1H, s), 8.37 (1H, s), 8.28-8.33 (2H, m), 8.11 (1H, d, J=8.56 Hz), 7.87 (1H, s), 7.54-7.63 (2H, m), 7.28 (1H, d, J=2.27 Hz), 6.88 (1H, dd, J=8.69, 2.14 Hz), 4.11 (2H, t, J=6.29 Hz), 3.59 (4H, br. s.), 2.45 (2H, br. s.), 2.32-2.45 (4H, m), 1.96 (2H, br. s.).

Provenance & Evidence