Pyridine → [5-(1-Methoxy-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]carbamic acid 2,2,2-trichloro-ethyl ester

온도

-15 °C

To an ice-salt cooled solution of 5-(1-methoxy-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (Preparation 11, 2.43 g, 10 mmol) and pyridine (0.9 mL, 11 mmol) in THF (30 mL), add a solution of 2,2,2-trichloroethylchloroformate (2.12 g, 10 mmol) in THF (10 mL) dropwise. Stir at −15° C. for 0.5 hour, then at 22° C. for 1 hour. Partition the reaction mixture between dichloromethane (50 mL) and saturated aq. sodium bicarbonate (50 mL). Isolate the aqueous phase and extract twice with dichloromethane (25 mL each). Dry the combined organic phases over sodium sulfate and concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give a white solid (3.73 g, 89% yield, ES+(m/z) 418.1 [M+H]).

1. waitat 22° C. for 1 hour
2. customPartition the reaction mixture between dichloromethane (50 mL) and saturated aq. sodium bicarbonate (50 mL)
3. customIsolate the aqueous phase
4. extractionextract twice with dichloromethane (25 mL each)
5. dry with materialDry the combined organic phases over sodium sulfate
6. concentrationconcentrate
7. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate
8. customto give a white solid (3.73 g, 89% yield, ES+(m/z) 418.1 [M+H])

ORD 기록

ord-1c0f4660d90c4e9a8523e9f28272863a

출처 데이터셋

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07582638B2