Methanamine, N-methoxy-, hydrochloride (1:1) → 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide

Temperatur

0 °C

To an oven-dried flask under a nitrogen atmosphere was added N,O-dimethylhydroxylamine hydrochloride (2.8 g, 28.6 mmol) to which a solution of trimethylaluminum (2.0 M in toluene, 14.3 mL, 28.6 mmol) was added at 0° C. and stirred for 30 min. Ethyl 5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step A, 4.0 g, 14.3 mmol) was added and the resulting solution was stirred at 23° C. for 4 h. The reaction mixture was cooled to 0° C. and carefully quenched by the dropwise addition of water (2 mL). Dichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which was then stirred for 20 min. at 23° C. The mixture was dried (Na2SO4 and MgSO4) and concentrated under reduced pressure to obtain the title compound (3.7 g) as an orange solid.

1. additionwas added at 0° C.
2. stirringthe resulting solution was stirred at 23° C. for 4 h
3. customcarefully quenched by the dropwise addition of water (2 mL)
4. additionDichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which
5. stirringwas then stirred for 20 min. at 23° C
6. dry with materialThe mixture was dried (Na2SO4 and MgSO4)
7. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-8c6f69353a0247be87b913c5791254fd

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09302999B2