Triethylamine → N-(2,6-dichloropyridin-4-yl)pivalamide

2,6-Dichloro-4-pyridinamine (10 g, 61.3 mmol) (Aldrich) and triethylamine (10.69 ml, 77 mmol) were combined in dichloromethane (DCM) (75 ml) and cooled in an ice-bath. 2,2-dimethylpropanoyl chloride (8.30 ml, 67.5 mmol) (Aldrich) in DCM (15 ml) was added drop wise and the mixture stirred whilst allowing to warm up overnight producing a clear dark orange solution. LCMS showed good conversion to product. The solution was washed with water and sat. NaHCO3 (100 ml each), dried with Na2SO4, filtered and concentrated to yield a dark orange solid. The crude product was taken up in the minimum of DCM and applied to a 320 g Companion XL silica column and eluted with 0% EtOAc in cyclohexane for 2 CVs then 0-15% EtOAc in cyclohexane over 12 CVs then held at 15% for 2 CV. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (11.59 g).

1. temperaturecooled in an ice-bath
2. temperatureto warm up overnight
3. customproducing a clear dark orange solution
4. washThe solution was washed with water and sat. NaHCO3 (100 ml each)
5. dry with materialdried with Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield a dark orange solid
9. washeluted with 0% EtOAc in cyclohexane for 2 CVs
10. customevaporated

ORD record

ord-955dd28129ce4ae2a1fd2003c95437cc

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633319B2