Triethylamine → HCID 178514441, compound

To a solution of cis/trans-4-(pyrimidin-4-yloxy)-cyclohexanecarboxylic acid (1:1) (0.750 g, 3.37 mmol) and triethylamine (0.470 ml, 3.37 mmol) in THF (16 ml) was added ethyl chloroformate (0.322 ml, 3.37 mmol) at 0° C. The reaction mixture was stirred for 1 h. The ammonium salts were removed by filtration. The filtrate was added to a cold solution of hydrazine hydrate (0.338 g, 6.75 mmol) in methanol (20 ml). The reaction mixture was stirred for 2 h at room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (100 ml) and a 1:1 mixture of 1 M aqueous sodium hydroxide solution and brine (30 ml). The organic layer was separated. The aqueous layer was extracted with three 100-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (0.588 g, 74%) as off-white solid, which was used in the next step without further purification.

1. customThe ammonium salts were removed by filtration
2. stirringThe reaction mixture was stirred for 2 h at room temperature
3. customThe solvent was evaporated under reduced pressure
4. customthe residue was partitioned between ethyl acetate (100 ml)
5. additiona 1:1 mixture of 1 M aqueous sodium hydroxide solution and brine (30 ml)
6. customThe organic layer was separated
7. extractionThe aqueous layer was extracted with three 100-ml portions of ethyl acetate
8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo

ORD record

ord-81bd7afe01df4859bb65cad75dd43888

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227458B2