Ammonium Chloride → HCID 90029584, compound

To a solution of 4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-3-carboxylic acid (compound 280.4, 5 g, 18.4 mmol) in N,N-dimethylformamide (50 mL) were added EDC.HCl (7 g, 36.5 mmol), NH4Cl (1.97 g, 36.8 mmol) and 4-dimethylaminopyridine (8.95 g, 73.3 mmol). The mixture was stirred for 2 h at room temperature, then warmed to 50° C. for 3 h. The reaction mixture was quenched with 30 mL of NH4Cl (sat). The aqueous phase was extracted with 2×100 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of NH4Cl (sat), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:5) as the eluent to furnish 1.3 g (26%) of the title compound.

1. temperaturewarmed to 50° C. for 3 h
2. customThe reaction mixture was quenched with 30 mL of NH4Cl (sat)
3. extractionThe aqueous phase was extracted with 2×100 mL of ethyl acetate
4. washThe combined organic layers were washed with 3×100 mL of NH4Cl (sat)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:5) as the eluent

ORD record

ord-f675b4412bd44497b5d20c4692e1709a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2