Dichloromethane → HCID 178432140, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(3-((cis-3-aminocyclobutyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one hydrochloride (Example 435; 20.6 mg, 0.052 mmol), methylvinylsulfone (Aldrich; 0.018 mL, 0.207 mmol), and DIPEA (0.036 mL, 0.207 mmol) in IPA (1.0 mL) was heated in a sealed vial at 120° C. for 15 min. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 100% EtOAc, then 0-10% (2M NH3 in MeOH)/DCM) to provide 2-(2-methyl-3-((cis-3-((2-(methylsulfonyl)ethyl)amino)cyclobutyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (20.5 mg, 0.044 mmol, 85% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.33 (1H, br. s.), 7.90 (1H, dd, J=7.5, 1.1 Hz), 7.56 (1H, dd, J=8.1, 1.1 Hz), 7.36 (1H, d, J=5.0.7 Hz), 7.32 (1H, t, J=7.8 Hz), 7.10 (1H, d, J=2.0 Hz), 6.95 (1H, s), 4.11-4.22 (1H, m), 3.46 (2H, td, J=6.8, 2.4 Hz), 3.28-3.30 (1H, m), 3.19-3.25 (2H, m), 3.05-3.15 (1H, m), 3.02 (3H, s), 2.92 (4H, t, J=6.7 Hz), 2.73-2.82 (2H, m), 2.55 (3H, s), 1.82-1.92 (2H, m). m/z (ESI, +ve) 469.0 (M+H)+.

Provenance & Evidence