Example 23
3-pyridinyl isocyanate (85 mg, mmol) was added to a solution of 3-(piperidin-4-ylmethyl)quinolone (150 mg, mmol) dissolved in THF (10 mL) and stirred overnight. The reaction was quenched with 1 N HCl (10 mL) and stirred for 5 minutes. The reaction was neutralized by addition of Na2CO3 and extracted three times with EtOAc. The product was run on a column of 9:1 DCM:MeOH yielding the product as an off-white solid (mg, mmol, %). MP=181.4-190.9° C. (188.2° C.) 1H NMR (300 MHz, DMSO-d6) δ 8.78 (d, J=2.2 Hz, 1H), 8.67-8.59 (m, 2H), 8.12 (dd, J=4.6, 1.5 Hz, 2H), 7.99 (d, J=7.8 Hz, 1H), 7.91 (d, J=8.2 Hz, 1H), 7.86 (ddd, J=8.4, 2.6, 1.5 Hz, 1H), 7.70 (ddd, J=8.4, 6.8, 1.5 Hz, 1H), 7.58 (ddd, J=8.1, 6.8, 1.3 Hz, 1H), 7.23 (dd, J=8.0, 4.6 Hz, 1H), 4.11 (d, J=13.6 Hz, 2H), 2.74 (dd, J=8.8, 4.6 Hz, 4H), 1.96-1.79 (m, 1H), 1.62 (d, J=11.5 Hz, 2H), 1.18 (qd, J=12.2, 3.9 Hz, 2H).
