Diisopropylethylamine → HCID 69675680, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-6-chloropyrimidine-5-carbonitrile (0.068 g, 0.440 mmol), 1-(6-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3-(pyridin-2-yl)quinolin-2-yl)-ethanamine (0.1536 g, 0.440 mmol), and n,n-diisopropylethylamine (0.383 mL, 2.198 mmol) in 1-butanol (4.40 mL) was stirred at 120° C. After 14.5 h, the mixture was removed from the heat and to the cooled mixture was added water (50 mL) and DCM (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the crude material. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 50% DCM:MeOH:NH4OH (89:9:1) in DCM, to provide a tan solid. The tan solid was suspended in DCM-hexane (1:1) and filtered to give 4-amino-6-((1-(6-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3-(2-pyridinyl)-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.55-8.62 (1H, m), 8.27 (1H, dd, J=9.2, 5.5 Hz), 7.86-7.93 (2H, m), 7.76-7.85 (2H, m), 7.58 (1H, d, J=7.0 Hz), 7.44-7.51 (1H, m), 7.37 (1H, ddd, J=7.6, 4.9, 1.0 Hz), 7.23 (2H, br. s.), 5.55 (1H, quin, J=6.7 Hz), 2.38 (3H, s), 1.39 (3H, d, J=6.7 Hz); LC-MS (ESI) m/z 468.1 [M+H]+.

Provenance & Evidence