Methanesulfonyl chloride → HCID 46842155, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.026 mL, 0.33 mmol) was added to a mixture of 3-(4-aminophenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one (0.11 g, 0.33 mmol) and TEA (0.093 mL, 0.67 mmol) in CH2Cl2 (5 mL). The mixture was stirred for 2 hours and concentrated in vacuo. The residue was redissolved in 1:1 dioxane and H2O (5 mL) and LiOH.H2O (0.050 g, 1.2 mmol) was added. The mixture was stirred at room temperature for 20 minutes, then extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was conducted by flash chromatography on silica gel, eluting with 10% to 80% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, followed by further purification by reverse-phase chromatography, eluting with 10% to 50% CH3CN in H2O with 0.1% TFA. The desired fractions were basified and extracted to afford the title compound as a white solid (0.075 g, 56%). 1H-NMR (300 MHz, DMSO-d6): δ9.91 (s, 1H), 8.43 (s, 1H), 8.20 (d, J=8.0 Hz, 1H), 7.85-7.98 (m, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.54-7.69 (m, 2H), 7.33 (d, J=8.7 Hz, 2H), 7.05-7.22 (m, 3H), 2.97 (s, 3H), 2.39 (s, 3H). MS (APCI) m/z: 407 (M+H)+.

Provenance & Evidence