Triethylamine → Tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate

Temperature

60 °C

A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (60 g, 271 mmol) in anhydrous N,N-dimethylformamide (600 mL) was cooled to 0° C. Triethylamine. (44.8 mL, 326 mmol) was added drop wise followed by tert-butyl 2-aminoethylcarbamate (52.2 g, 326 mmol). After 30 minutes the ice bath was removed and the reaction mixture was heated to 60° C. The reaction was heated at 60° C. overnight and then it was concentrated under reduced pressure to provide an orange oil. The oil was dissolved in ethyl acetate (1 L), washed with water (3×500 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellow oil. The oil was triturated with methanol (˜100 mL). The resulting solid was isolated by filtration and washed with cold methanol to provide 72.3 g of tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate as a solid.

1. addition(44.8 mL, 326 mmol) was added drop
2. customAfter 30 minutes the ice bath was removed
3. temperatureThe reaction was heated at 60° C. overnight
4. concentrationit was concentrated under reduced pressure
5. customto provide an orange oil
6. washwashed with water (3×500 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto provide a yellow oil
10. customThe oil was triturated with methanol (˜100 mL)
11. customThe resulting solid was isolated by filtration
12. washwashed with cold methanol

ORD record

ord-9e68e54d9c07451db77120fd3e081e1d

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720422B2