Triethylamine → HCID 178521183, compound

Participants

Reaction Steps

To a solution of EDCl (0.22 g, 1.17 mmol), HOBT (0.16 g, 1.17 mmol) in 10 mL of DMF were added [4-(6-fluoro-1H-indazol-3-yl)-piperidin-1-yl]-acetic acid (0.27 g, 1.0 mmol), 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (0.19 g, 1.1 mmol), and Et3N (0.40 g, 3.9 mmol). The reaction mixture was stirred at ambient temperature for 15 hours then poured into a separatory funnel containing brine. After separation, the aqueous layer was extracted with DCM (50 mL). The combined organic layers were washed with saturated aqueous NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo to yield an oily liquid. Purification by flash chromatography gave the title compound (89.0 mg, 0.19 mmol, 20% yield) as a yellow solid. MS (ESI) m/z 440.8 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 0.96 min. 1H NMR (400 MHz, MeOD) δ ppm 1.94-2.27 (m, 4H), 2.36-2.56 (m, 2H), 2.64 (br. s., 2H), 2.98-3.46 (m, 4H), 3.90 (br. s., 2H), 4.27-4.59 (m, 2H), 4.72-5.01 (m, 3H), 6.91 (br. s., 1H), 7.14 (br. s., 1H), 7.82 (br. s., 1H). HRMS calculated for C22H26FN6O3: 441.2050 (M+H). found (ESI, [M+H]+): 441.2067.

Provenance & Evidence