4-(2-Aminoethyl)benzenesulfonamide → 3'-[{2-[4-(aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

4-(2-Aminoethyl)benzene sulfonamide (2.37 g) and molecular sieves 3A (4.0 g) were added to a solution of 3′-formyl-N-[2-(1-pyrrolidinyl)ethyl][1,1′-biphenyl]-3-carboxamide (3.81 g) in methanol (50 ml), and the mixture was stirred at room temperature for 1.5 hours. After the reaction mixture was diluted with tetrahydrofuran (THF), the molecular sieves were filtered off, and the filtrate was concentrated under reduced pressure. The residues were dissolved in a mixed solvent (100 ml) of methanol-THF (1:1), and sodium borohydride (0.89 g) was added thereto. The reaction mixture was stirred at room temperature for 5 hours, and then the solvent was evaporated under reduced pressure. The residues were diluted with water and extracted with ethyl acetate. The extract was washed with brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residues were crystallized from hexane, whereby the title compound (3.71 g) was obtained.

1. filtrationthe molecular sieves were filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe residues were dissolved in a mixed solvent (100 ml) of methanol-THF (1:1), and sodium borohydride (0.89 g)
4. additionwas added
5. stirringThe reaction mixture was stirred at room temperature for 5 hours
6. customthe solvent was evaporated under reduced pressure
7. additionThe residues were diluted with water
8. extractionextracted with ethyl acetate
9. washThe extract was washed with brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residues were crystallized from hexane, whereby the title compound (3.71 g)
13. customwas obtained

ORDレコード

ord-c113ed0e9c5f49ae997f36f353ec3220

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091247B2