Ammonia → HCID 66604175, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 7-((2S,6R)-2,6-dimethylmorpholino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (16 mg, 0.033 mmol) in 7 N NH3 in MeOH (5 mL) in a sealed microwave vial was heated at 80° C. for 48 hr. Removal of the solvent followed by preparative HPLC (100×30 mm Luna C18 column, gradient elution with A:B=75:25 to A:B=25:75 [A=95% H2O:5% MeOH:0.1% TFA; B=5% H2O:95% MeOH:0.1% TFA] over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 7-((2S,6R)-2,6-dimethylmorpholino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (12.9 mg, 0.026 mmol, 79% yield) as an orange solid. MS (ESI) m/z 469.28 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.47 (1H, s), 8.39 (1H, t, J=4.27 Hz), 8.23 (1H, d, J=8.55 Hz), 8.20 (1H, s), 7.72(2H, d, J=4.27 Hz), 7.07-7.11 (1H, m), 7.01-7.08 (1H, m), 3.80-3.91 (2H, m), 3.70-3.76 (2H, m), 2.43-2.53 (2H, m), 1.29 (6H, d, J=6.41 Hz).

Provenance & Evidence