2-(Trimethylsilyl)ethanol → Tert-butyl 4-(1-(3,4-dichlorophenyl)-6-oxo-3-((2-(trimethylsilyl)ethoxy)carbonylamino)-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirring solution of 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (from example 15 step A) (48 mg, 0.10 mmol) in dioxane (10 mL) at room temperature under argon was added diphenyl phosphorazidate (65 mg, 0.20 mmol) and TEA (51 mg, 0.50 mmol). The resulting reaction mixture was stirred at room temperature for 1 hour, then 2-(trimethylsilyl)ethanol (118 mg, 1.0 mmol) was added. The resulting reaction mixture was heated at 80° C. under argon overnight. Solvent was concentrated. Crude reaction mixture was used directly to next step. MS (ESI) 597 (M−H).

Provenance & Evidence