Water → HCID 53251828, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanamine (300 mg, 0.86 mmol) and 4-amino-6-chloropyrimidine-5-carbonitrile (135 mg, 0.86 mmol) in n-butanol (5.2 mL) was added diisopropylethyl amine (336 mg, 2.6 mmol) at 25° C. The reaction mixture was stirred for overnight at 110° C. Water was added to the reaction mixture and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated it. The residue was purified by column chromatography on neutral alumina using 0-5% MeOH in DCM. It was further purified by reversed-phase HPLC to give 4-amino-6-((1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)amino)-5-pyrimidinecarbonitrile: 1H NMR (400 MHz, DMSO-d6): δ 1.380 (d, 3H, J=6.8 Hz), 3.215 (s, 3H), 5.240-5.310 (m, 1H), 7.256 (br s, 2H), 7.718-7.828 (m, 2H), 7.934-7.950 (m, 3H), 8.123 (dd, 1H, J=1.2 Hz, 7.6 Hz), 8.336 (dd, 1H, J=2.4 Hz, 9.6 Hz). 8.678 (s, 1H), 9.117 (d, 1H, J=2.8 Hz); LC-MS (ESI) m/z 464.2 [M+H]+.

Provenance & Evidence