Diisopropylethylamine → N-((4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)phenyl)carbamoyl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 59a (100 mg, 0.147 mmol) and ethyl methylsulfonylcarbamate (148 mg, 0.888 mmol) and DIEA (0.191 mL, 1.11 mmol) in DMF (2 mL) was stirred at 100° C. for 2 h. The reaction mixture was allowed to cool to rt and diluted with DCM. The reaction mixture was concentrated and the residue obtained was purified by flash column chromatography on silica gel (0-20% MeOH/EtOAc), recrystallized with EtOAc/heptanes and purified by prep-TLC (1:5:5 MeOH/DCM/EtOAc) to give the title compound 40. 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.22-3.30 (m, 2H), 3.33 (s, 3H), 3.37-3.47 (m, 2H), 3.69-3.87 (m, 4H), 4.03-4.21 (m, 4H), 7.16 (s, 1H), 7.31 (s, 1H), 7.28 (s, 1H), 7.39 (d, J=8.3 Hz, 1H), 7.43-7.60 (m, 3H), 7.67-7.76 (m, 1H), 7.82 (d, J=7.6 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 8.15 (d, J=8.3 Hz, 1H), 8.81 (br. s., 1H). Mass Spectrum LCMS, ESI (pos.) Calcd. for C29H29N7O4S: 572.2 [M+H]. found 572.5.

Provenance & Evidence