Triethylamine → HCID 178514445, compound

To a solution of cis/trans-4-(pyrimidin-2-yloxy)-cyclohexanecarboxylic acid (1:2) (0.258 g, 1.16 mmol) and triethylamine (0.162 ml, 1.16 mmol) in THF (6 ml) was added ethyl chloroformate (0.111 ml, 1.16 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 (0.116 g, 2.32 mmol) in methanol (10 ml). The reaction mixture was stirred for 2 h at room temperature and then partitioned between ethyl acetate (50 ml) and a mixture of a 1:1 mixture of 1 M aqueous sodium hydroxide solution and brine (50 ml). The layers were separated. The aqueous layer was extracted with five 50-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 (0.177 g, 65%) as 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. custompartitioned between ethyl acetate (50 ml)
4. additiona mixture of a 1:1 mixture of 1 M aqueous sodium hydroxide solution and brine (50 ml)
5. customThe layers were separated
6. extractionThe aqueous layer was extracted with five 50-ml portions of ethyl acetate
7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-8cdcc53bf34246489ade4cb22644c625

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461152B2