Water → HCID 90418711, compound

In a 100 mL round bottom flask, methyl 4-amino-6-(benzo[b]thiophen-5-yl)-3,5-dichloropicolinate (210 mg, 0.595 mmol) was dissolved in methanol (2.3 mL), tetrahydrofuran (2.3 mL), and H2O (1.2 mL). Lithium hydroxide hydrate (74.8 mg, 1.784 mmol) was added as a solid. The reaction was stirred at room temperature until complete. The reaction mixture was concentrated to dryness. The resulting residue was dissolved in H2O (2.0 mL) and 1 N HCl was used to adjust the pH to 3.0, causing a precipitate to form. This suspension was extracted with ethyl acetate (3×15 mL). The organic extracts were combined, washed with Saturated NaCl solution, dried (MgSO4), filtered and concentrated. Additional purification of the resulting solid was performed, as needed, using a Teledyne ISCO reverse phase system with a gradient eluent system of acetonitrile and H2O to yield the title compound as a white solid (110 mg, 55.

1. concentrationThe reaction mixture was concentrated to dryness
2. dissolutionThe resulting residue was dissolved in H2O (2.0 mL)
3. customto form
4. extractionThis suspension was extracted with ethyl acetate (3×15 mL)
5. washwashed with Saturated NaCl solution
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customAdditional purification of the resulting solid

ORD record

ord-7fd3b66a329c4203ab507daeed75db76

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278985B2