Triethylamine → HCID 11784952, compound

Participants

Reaction Steps

The product from Step 4 (0.250 g, 0.46 mmol) was dissolved in MeOH (5 mL) and 2N HCl (3 mL). To the solution was added NaNO2 (0.065 g, 0.92 mmol), and the mixture was allowed to stir at rt for 30 min. The reaction mixture was concentrated, then dissolved in THF (3 mL). Triethylamine (0.25 mL), and NH2OH (50% aqueous solution, 0.07 mL) were added and the mixture was heated in a sealed tube to 90° C. for 1 hour. The reaction mixture was then cooled, poured into EtOAc and washed with H2O. The organic layer was dried over MgSO4, filtered, then concentrated in-vacuo to give a dark oil. The oil was dissolved in dioxane (3 mL) and Et3N (0.5 mL) and the reaction mixture was heated in a sealed tube to 150° C. for 1 hour. The mixture was then cooled, and concentrated in-vacuo. The crude oil was dissolved in dichloromethane (2 mL) and to the solution was added 4N HCl in dioxane and the resulting solution was allowed to stir at rt for 30 min. The mixture was then concentrated in-vacuo, and the oil was dissolved in a minimal amount of MeOH then poured into Et2O to afford the title compound as a tan solid (40 mg, 18%). MS (ES+) m/e 484 [M+H]+.

Provenance & Evidence