1-(2-Amino-3,5-dimethylphenyl)ethan-1-one → HCID 9934302、化合物

To a solution of 2′-amino-3′,5′-dimethylacetophenone (1.9 g, 11.66 mmol) in dichloromethane (20 mL) at room temperature was added N-(4-chloro-3-methyl-5-isoxazolyl)-N-methoxymethyl-3-sulfamoyl-2-thiophenecarbonyl chloride (Example 51) (1 g, 2.86 mmol). The mixture was stirred for 10 h during which much yellow precipitate formed. The reaction was then concentrated and the residue was diluted with ethyl acetate (50 mL) and washed with 1 N HCl (50 mL). The organic layer was concentrated and the residue was dissolved in methanol (30 mL) followed by the addition of concentrated HCl (15 mL). The mixture was then heated under reflux for 2 h before it was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with water (2×200 mL). The organic layer was separated, dried (MgSO4), the solids filtered and the filtrate concentrated. The residue was then purified by reverse phase HPLC to give N-(2-acetyl-4,6-dimethylphenyl)-3-(((4-chloro-3-methyl-5-isoxazolyl)amino)sulfonyl)-2-thiophenecarboxamide (580 mg, 43%).

1. customformed
2. concentrationThe reaction was then concentrated
3. additionthe residue was diluted with ethyl acetate (50 mL)
4. washwashed with 1 N HCl (50 mL)
5. concentrationThe organic layer was concentrated
6. dissolutionthe residue was dissolved in methanol (30 mL)
7. additionfollowed by the addition of concentrated HCl (15 mL)
8. temperatureThe mixture was then heated
9. temperatureunder reflux for 2 h before it
10. additiondiluted with ethyl acetate (200 mL)
11. washwashed with water (2×200 mL)
12. customThe organic layer was separated
13. dry with materialdried (MgSO4)
14. filtrationthe solids filtered
15. concentrationthe filtrate concentrated
16. customThe residue was then purified by reverse phase HPLC

ORDレコード

ord-9558ef6296c940d6bb665eba4aa13610

出典データセット

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06683103B2