N,N'-Dimethylethylenediamine → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

Temperatur

80 °C

A 100-mL, 3-neck round bottom flask was charged with copper(I) chloride (59.6 mg, 0.602 mmol) and acetonitrile (10 mL), N,N′-dimethyethane-1,2-diamine (106 mg, 1.203 mmol) was added and the mixture was stirred under nitrogen to afford a solution. N-(3-Chloro-1H-pyrazol-4-yl)acetamide (480 mg, 3.01 mmol) and potassium carbonate (831 mg, 6.02 mmol) were added, followed by 3-bromopyridine (570 mg, 3.61 mmol). The mixture was purged with nitrogen three times and heated at 80° C. for 18 hours. Thin layer chromatography analysis [Eluent: ethyl acetate, SM Rf=0.5, Product Rf=0.3] indicated that a trace of starting material remained and a major product formed. It was filtered through a pad of Celite® and the Celite® pad rinsed with acetonitrile (10 mL). The combined filtrates were concentrated to about 5 mL and water (10 mL) was added to the resulting suspension. The suspension was stirred for 1 hour and filtered. The solid was rinsed with water (2×5 mL) and dried under vacuum at room temperature to afford a white solid (458 mg, 64%). Characterization matched sample prepared by previous method.

1. additionwas added
2. customto afford a solution
3. customThe mixture was purged with nitrogen three times
4. customa major product formed
5. filtrationIt was filtered through a pad of Celite®
6. washthe Celite® pad rinsed with acetonitrile (10 mL)
7. concentrationThe combined filtrates were concentrated to about 5 mL and water (10 mL)
8. additionwas added to the resulting suspension
9. stirringThe suspension was stirred for 1 hour
10. filtrationfiltered
11. washThe solid was rinsed with water (2×5 mL)
12. customdried under vacuum at room temperature

ORD-Eintrag

ord-d4aaccc138be48dd86f8b6ada734e848

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09102655B2