Triethylamine → N-({[2-(4-{2-Ethyl-5-[1-(methyloxy)ethyl]-1H-benzimidazol-1-YL]phenyl)ethyl]amino}carbonyl)-4-methylbenzenesulfonamide

A solution of N-{[(2-{4-[2-ethyl-5-(1-hydroxyethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide (Example 345, 151 mg, 0.3 mmol) in CH2Cl2 (15 ml) was added thionyl chloride (0.1 ml, 1.5 mmol) at room temperature. The mixture was stirred at room temperature for 2 h. The solvent was removed and the residue was dissolved with methanol (15 ml). The mixture was added triethylamine (0.08 ml, 0.6 mmol) and stirred at room temperature for 5 h. The solvent was removed and the residue was extracted with CH2Cl2 (50 ml). The organic layer was washed with water(10 ml), brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (1:6)/CH2Cl2:methanol(10:1) to afford 139 mg (89%) of the title compound as white solids.

1. customThe solvent was removed
2. dissolutionthe residue was dissolved with methanol (15 ml)
3. stirringstirred at room temperature for 5 h
4. customThe solvent was removed
5. extractionthe residue was extracted with CH2Cl2 (50 ml)
6. washThe organic layer was washed with water(10 ml), brine (10 ml)
7. dry with materialdried (Na2SO4)
8. customAfter removal of solvent
9. customthe crude product was purified by flash column chromatography
10. washeluting with hexane/ethyl acetate (1:6)/CH2Cl2:methanol(10:1)

ORDレコード

ord-3f7d3ab2f1734e7da356722ba36d739f

出典データセット

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07148234B2