Tetrabutylammonium Fluoride → Tert-butyl 4-(3-amino-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirring solution of tert-butyl 4-(1-(3,4-dichlorophenyl)-6-oxo-3-((2-(trimethylsilyl)ethoxy)carbonylamino)-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (60 mg, 0.10 mmol) in THF (10 ml) at room temperature under argon was added 1M TBAF in THF (1 mL, 1.0 mmol). The reaction mixture was stirred at room temperature overnight. Solvent was removed in vacuo. The crude product was directly purified by preparative HPLC (C18 column; 10-100% methanol in water without TFA) to give tert-butyl 4-(3-amino-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (28 mg, white solid, 55%). 1H NMR (400 MHz, CDCl3) δ ppm 1.34-1.55 (m, 9H) 1.65-1.91 (m, 2H) 2.04 (dd, J=12.96, 3.30 Hz, 2H) 3.06-3.39 (m, 2H) 3.59-3.94 (m, 2H) 4.29-4.71 (m, 2H) 6.20 (s, 1H) 7.43-7.50 (m, 1H) 7.54-7.64 (m, 1H) 7.80 (d, J=2.20 Hz, 1H). MS (ESI) 455 (M+H).

Provenance & Evidence