Reaction Steps
To a 1 dram vial was added (1R,2R)—N1-(1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (25 mg, 0.079 mmol), DMF (1 mL), diisopropyl ethyl amine (0.069 mL, 0.393 mmol) and 2-chlorobenzo[d]oxazole (0.013 mL, 0.118 mmol). The vial was capped and the reaction was stirred at 65° C. for 1 hr. After this time, the reaction was diluted with MeOH and purified using RP prep-HPLC. Two diastereomers were separated. The desired isomer had the shorter retention time. The fractions with the desired material were concentrated to give the product (1R,2R)—N1-(benzo[d]oxazol-2-yl)-N2-((S)-1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (16 mg, 0.036 mmol, 45.4% yield) as yellow solid. Anal. Calcd. for C24H29N5O3 m/z 435.5, found: 436.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.06-7.92 (m, 2 H), 7.37 (d, J=7.70 Hz, 1 H), 7.25-7.15 (m, 2 H), 7.06 (t, J=7.70 Hz, 1H), 6.65 (d, J=9.35 Hz, 2 H), 5.33-5.15 (m, 1 H), 3.67 (d, J=9.08 Hz, 1 H), 3.59 (d, J=11.28 Hz, 1 H), 3.44 (br. s., 1 H), 3.16-3.03 (m, 1 H), 2.89 (br. s., 2 H), 2.63 (br. s., 1 H), 2.40 (br. s., 1 H), 2.16 (d, J=11.28 Hz, 1 H), 2.00-1.91 (m, 1 H), 1.82 (d, J=9.63 Hz, 4 H), 1.71-1.58 (m, 3 H), 1.44 (d, J=9.35 Hz, 2 H); 13C NMR (126 MHz, CDCl3) δ ppm 162.09, 162.07, 154.71, 148.33, 126.15, 124.01, 121.2, 116.46, 112.55, 108.84, 59.37, 57.80, 53.01, 51.03, 48.07, 32.22, 31.92, 29.73, 24.84, 24.60, 22.91.
