Potassium Carbonate → HCID 57786190, Verbindung

To a solution of 4-[4-chloro-2-[(3,5-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol (Reference Example 42; 7.0 mg, 0.015 mmol) in pyridine (1.0 mL) was added methanesulfonyl chloride (0.050 mL, 0.064 mmol) dropwise at 0° C. The mixture was warmed to room temperature and stirred for 26 hr. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude mesylate was dissolved in N,N-dimethylformamide (1.0 mL) and potassium carbonate (11 mg, 0.077 mmol) was added. The mixture was stirred at 80° C. for 16 hr. Water was added and the mixture was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (6.1 mg, 0.014 mmol, 93%) as a colorless amorphous.

1. extractionthe mixture was extracted with ethyl acetate
2. washOrganic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. dissolutionThe resulting crude mesylate was dissolved in N,N-dimethylformamide (1.0 mL)
6. stirringThe mixture was stirred at 80° C. for 16 hr
7. extractionthe mixture was extracted with ethyl acetate
8. washOrganic layer was washed with water and brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography on silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture
12. concentrationThe filtrate was concentrated in vacuo

ORD-Eintrag

ord-e1969b6e3b23406ea7ac9bdf11bbdc6a

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08785460B2