Hydrochloric Acid → HCID 67025901, compound

Temperature

-30 °C

To a solution under nitrogen of 0.169 ml (1.2 mmol) of diisopropylamine in 2.5 ml of THF, maintained at −30° C., is added 0.75 ml (1.2 mmol) of n-butyllithium (1.6 M solution in hexane) over 10 minutes. After stirring for 15 minutes at −30° C., 0.172 ml (1.57 mmol) of 1,3-dimethyl-2-imidazolidinone is added, at −60° C., over 15 minutes. Next, 88.43 mg (1.09 mmol) of cyclobutanecarbonitrile dissolved in 0.75 ml of THF are added over 10 minutes, at −70° C. The orange solution obtained is stirred for one hour at −70° C., after which 245 mg (1.09 mmol) of the compound prepared in Example 1d dissolved in 0.75 ml of THF are added over 10 minutes. After stirring for 2 hours at −70° C., the orange reaction medium is poured into 15 ml of water, acidified with 1N HCl and extracted with ethyl ether. The organic phase is washed with water, dried over Na2SO4 and concentrated under vacuum to give a yellow oil. After purification by flash chromatography on silica gel, in dichloromethane, 141 mg of a pale yellow oil are obtained.

1. additionare added over 10 minutes, at −70° C
2. customThe orange solution obtained
3. stirringis stirred for one hour at −70° C.
4. additionare added over 10 minutes
5. stirringAfter stirring for 2 hours at −70° C.
6. extractionextracted with ethyl ether
7. washThe organic phase is washed with water
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under vacuum
10. customto give a yellow oil
11. customAfter purification by flash chromatography on silica gel

ORD record

ord-f3186c87d9414cbc84d4efc10f552381

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357721B2