Methylamine → HCID 86726460, compound

HATU (0.606 g, 1.594 mmol) was added to a solution of 6-methoxy-5-nitropicolinic acid (Preparation 190, 0.243 g, 1.226 mmol), DIPEA (0.320 mL, 1.840 mmol) and 2M methylamine solution in THF (1.2 mL, 2.453 mmol) in THF (3.3 mL). The reaction mixture was stirred at room temperature for 3 hours. Further methylamine (0.6 mL) was added and the mixture was stirred for 18 hours. The reaction was quenched with water and concentrated in vacuo. The aqueous phase was extracted with EtOAc (×2) and the combined organic layers were washed twice with water, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with DCM/EtOAc 99/1 to 90/10 to afford the title compound as a yellow solid (182 mg, 70%).

1. stirringthe mixture was stirred for 18 hours
2. customThe reaction was quenched with water
3. concentrationconcentrated in vacuo
4. extractionThe aqueous phase was extracted with EtOAc (×2)
5. washthe combined organic layers were washed twice with water
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by Biotage silica gel column chromatography
10. washeluting with DCM/EtOAc 99/1 to 90/10

ORD record

ord-89a71f696b014997bde2134d32a77073

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409907B2