1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one

Temperature

110 °C

Copper iodide (16 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (28.8 mg, 0.25 mmol) and potassium phosphate (445 mg, 2.1 mmol) were added to 1,4-Dioxane (10 mL) previously degassed with argon (10 minutes). The reaction mixture was purged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.84 mmol) and 2-bromo-5-methylthiophene (150 mg, 0.84 mmol). The resulting mixture was heated to reflux at 110° C. for 4 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through celite and the celitebed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. The concentrate was quenched with ice, the precipitate formed was collected and dried to afford 170 mg (74% yield) of 1-(4-methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one.

1. custompreviously degassed with argon (10 minutes)
2. customThe reaction mixture was purged with argon for a further 10 minutes
3. temperatureThe resulting mixture was heated
4. filtrationThe reaction mixture was filtered through celite
5. washthe celitebed was washed with chloroform
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated
8. customThe concentrate was quenched with ice
9. customthe precipitate formed
10. customwas collected
11. customdried

ORD record

ord-9d155cf1125b484f9d5ab50ed4b67e28

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE045173E1