Tert-Butylamine → HCID 118511961, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-(tert-Butylamino)-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one enantiomers were prepared similar to that described in Example 131 using rac-2-(3-fluoro-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 156; 69.4 mg, 0.224 mmol) and 2-methylpropan-2-amine (TCI America, Portland, Oreg.; 0.071 mL, 0.671 mmol) in DMSO (1.0 mL), heating 100° C. for 1.5 h. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished rac-2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (43.6 mg, 0.120 mmol, 54% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (1H, br. s.), 7.79 (1H, d, J=7.4 Hz), 7.59 (1H, d, J=8.2 Hz), 7.33 (1H, t, J=7.8 Hz), 6.95 (1H, s), 6.92 (1H, br. s.), 5.97 (1H, s), 3.45-3.55 (1H, m), 3.01-3.14 (2H, m), 2.55 (3H, s), 1.54 (9H, s), 1.27 (3H, d, J=6.3 Hz). m/z (ESI, +ve) 364.2 (M+H)+. Separation of this material by supercritical-fluid chromatography (Chiralpak AS-H (250×21 mm, 5 μm), 70% liquid CO2/30% MeOH (+20 mM NH3), 70 mL/min) separately afforded: 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, first-eluting enantiomer (162; 17.4 mg, 0.048 mmol) as a yellow solid; and 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, second-eluting enantiomer (163; 16.4 mg, 0.045 mmol) as a yellow solid.

Provenance & Evidence