Methane → HCID 66667734, compound

To a suspension of methyl 6-[(isobutyrylamino)methyl]nicotinate (Preparation 26, 935 mg, 3.96 mmol) in toluene (10 mL) was added phosphoryl chloride (3.03 g, 1.84 mL, 19.8 mmol) and the mixture refluxed under nitrogen for 3 hours. The resulting dark solution was cooled at room temperature and concentrated in vacuo to give an oil. The oil was then dissolved in toluene (10 mL) and concentrated in vacuo again. The resulting residue was partitioned between EtOAc (20 mL) and saturated aqueous sodium hydrogen carbonate solution (2×5 mL). The organic layer was washed with brine (5 mL), dried over magnesium sulfate, filtered and evaporated to yield a dark oil, which was dissolved in methanol (10 mL), treated with charcoal and refluxed for 5 minutes. The mixture was filtered through Celite and the filtrate concentrated in vacuo to yield the title compound as a pale yellow oil (830 mg, 82%), which was used directly in the next stage without further purification.

1. temperaturethe mixture refluxed under nitrogen for 3 hours
2. concentrationconcentrated in vacuo
3. customto give an oil
4. concentrationconcentrated in vacuo again
5. customThe resulting residue was partitioned between EtOAc (20 mL) and saturated aqueous sodium hydrogen carbonate solution (2×5 mL)
6. washThe organic layer was washed with brine (5 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customevaporated
10. customto yield a dark oil, which
11. temperaturerefluxed for 5 minutes
12. filtrationThe mixture was filtered through Celite
13. concentrationthe filtrate concentrated in vacuo

ORD record

ord-65b39f07952c4c14a49620b283d76f83

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2