1,2-Dichloroethane → HCID 21339390, compound

Temperature

0 °C

The tert-butyl ester from above (1 g, 3.47 mmol) was dissolved in 10 mL CH2Cl2 and 5 mL trifluoroacetic acid was added. The reaction mixture was stirred for 1 h. Solvents were evaporated and the residue was taken up in 2×10 mL CH2Cl2 and evaporated to an oil. In a separate flask, picolinic acid (470 mg, 3.82 mmol) was dissolved in 10 ML DMF and the resulting solution was cooled to 0° C. EDC (787 mg, 4.1 mmol) and HOBT (554 mg, 4.1 mmol) were added and the reaction mixture was stirred at 0° C. for 1 h. In a separate flask, the free amine prepared above was dissolved in 5 mL DMF and 1.5 mL N-methylmorpholine was added. This solution was added to the reaction mixture at 0° C. The reaction mixture was allowed to stir at ambient temperature for 16 h after which time it was poured into a mixture of ice/5% citric acid (100 mL) and extracted with 4×30 mL EtOAc. The combined EtOAc extracts were washed with 3×100 mL brine, 2×100 mL NaHCO3, 1×100 mL brine, dried with Na2SO4, and evaporated to an oil which was dried under vacuum yielding 990 mg (100%) of pyridine-2-carboxylic acid [1-(N-methoxy-N-methylcarbamoyl)-3-methylbutyl]amide. This was used without further purification.

1. customSolvents were evaporated
2. customevaporated to an oil
3. stirringthe reaction mixture was stirred at 0° C. for 1 h
4. additionThis solution was added to the reaction mixture at 0° C
5. stirringto stir at ambient temperature for 16 h after which time it
6. extractionextracted with 4×30 mL EtOAc
7. washThe combined EtOAc extracts were washed with 3×100 mL brine, 2×100 mL NaHCO3, 1×100 mL brine
8. dry with materialdried with Na2SO4
9. customevaporated to an oil which
10. customwas dried under vacuum

ORD record

ord-1d67ab0bc7ae41e5946f52750e25288a

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608057B2