Methanol → HCID 67248245, compound

Temperature

50 °C

To a stirred solution of 5-amino-4-methylpyridine-3-carboxylic acid (0.94 g, 6.18 mmol) in MeOH (20 ml at 0° C. was added thionyl chloride drop-wise. The solution was then heated to 50° C. for 3.5 h, a further 10 ml of MeOH was added and the reaction heated at 50° C. for 5 h followed by stirring at room temperature for 64 h. The solvent was then evaporated under reduced pressure and saturated NaHCO3 solution was added until pH7-8. The product was extracted into EtOAc (2×50 ml) and the combined organics were washed with brine (50 ml) dried using Na2SO4, filtered and evaporated to afford the title compound as an off-white powder (824 mg, 80%) which was suitable for use in the next stage without any purification. LC-MS m/z=167.0, 1H NMR (500 MHz, Chloroform-d) δ 8.52 (d, J=34.2 Hz, 1H), 8.16 (s, 1H), 3.95 (d, J=4.8 Hz, 3H), 3.78 (s, 2H), 2.42 (s, 3H).

1. temperaturethe reaction heated at 50° C. for 5 h
2. customThe solvent was then evaporated under reduced pressure and saturated NaHCO3 solution
3. additionwas added until pH7-8
4. extractionThe product was extracted into EtOAc (2×50 ml)
5. washthe combined organics were washed with brine (50 ml)
6. customdried
7. filtrationfiltered
8. customevaporated

ORD record

ord-9ba4fda264aa469d9687bcf3b061be67

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2