Methanesulfonamide → HCID 58042386, compound

Temperature

60 °C

To a suspension of methanesulfonamide (93.4 mg, 0.98 mmol) in THF (2 mL) at room temperature was added potassium tert-butoxide (119 mg, 1.06 mmol) in one portion with stirring under nitrogen for 15 minutes. 4-Methylphenyl-5-chloro-4-[(5-chloro-6-isopropoxypyridin-3-yl)thio]-2-fluorobenzoate (Preparation 224, 352 mg, 0.75 mmol) was added as a solution in THF (2 mL). The mixture was then heated at 60° C. for 3 hours and then left at room temperature for 18 hours. The solvent was concentrated in vacuo and the residue was partitioned between EtOAc (10 mL) and water (5 mL). The organic layer was separated and then washed with 1M NaOH (5 mL), 2M HCl (5 mL), saturated aqueous brine (5 mL), dried over MgSO4 filtered and evaporated. The residue was triturated with acetone/heptane (1:9) to afford a white solid which was filtered and washed with heptane to yield the title compound (45 mg, 13%) as a white solid.

1. waitleft at room temperature for 18 hours
2. concentrationThe solvent was concentrated in vacuo
3. customthe residue was partitioned between EtOAc (10 mL) and water (5 mL)
4. customThe organic layer was separated
5. washwashed with 1M NaOH (5 mL), 2M HCl (5 mL), saturated aqueous brine (5 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customThe residue was triturated with acetone/heptane (1:9)
10. customto afford a white solid which
11. filtrationwas filtered
12. washwashed with heptane

ORD record

ord-639a9398898f4b87ab0f1a054384d22e

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2