Multi-step reaction with 7 steps
1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
4: sodium hydroxide / methanol / 20 °C / Inert atmosphere
5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
6: dichloromethane / 1 h / Inert atmosphere
7: triethylamine / acetonitrile / 16 h / 20 °C / Inert atmosphere
With
dimethylsulfide borane complex; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/acs.jmedchem.5b01801