4-Methylmorpholine → HCID 10449448, compound

Participants

Reaction Steps

A solution of Example 3C (0.10 g, 0.33 mmol), (1S,2R)-1-amino-2-hydroxyindane (0.086 g, 0.58 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.080 g, 0.41 mmol), 1-hydroxybenzotriazole (0.061 g, 0.45 mmol), and N-methylmorpholine (0.05 mL, 0.46 mmol) in 3:1 dichloromethane/DMF (4 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 4M HCl in dioxane (3 mL), stirred for 1 hour, concentrated, then purified by reverse phase HPLC with acetonitrile/water to provide the desired product. MS (ESI) m/e 333 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.81 (br s, 2H), 7.40–7.17 (m, 4H), 6.65 (d, 1H), 5.52 (m, 1H), 4.18 (d, 1H), 3.14 (m, 1H), 2.55–2.45 (m, 2H), 1.80–1.67 (m, 5H), 1.57–1.51 (m, 1H), 1.46–1.17 (m, 5H), 1.00–0.90 (m, 2H).

Provenance & Evidence