1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Methoxy-N,2,6-trimethyl-N-(2-(2-oxo-2-(2-(piperidin-1-yl-methyl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethoxy)ethyl)benzene-sulfonamide

2-(2-(4-Methoxy-N,2,6-trimethylphenylsulfonamido)ethoxy)acetic acid (AC6) (353 mg, 1.06 mmol), diisopropylethylamine (372 μl, 2.13 mmol), HOAt (15 mg, 107 μmol) and EDCI (306 mg, 1.60 mmol) were added to a solution of 2-(piperidin-1-ylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (TP10) (277 mg, max. 425 μm) in MC (25 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then concentrated in vacuo and the residue obtained was purified by chromatography on silica gel (MC/(7 M NH3 in MeOH), 98:2 and 99:1). The product fractions were combined and evaporated to dryness. The residue was dissolved in dry acetonitrile (5 ml), the solution was dried by freeze drying and the solid was then dissolved in methylene chloride (10 ml). Solid NaHCO3 (approx. 500 mg) was added to this solution and the mixture was stirred for 1 hour. The mixture was then filtered and the filtrate was concentrated in vacuo. The yield was 105 mg (45% over 2 stages). MS, Rt=3.0 min, m/z=550.1 [MH]+

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customthe residue obtained
3. customwas purified by chromatography on silica gel (MC/(7 M NH3 in MeOH), 98:2 and 99:1)
4. customevaporated to dryness
5. dissolutionThe residue was dissolved in dry acetonitrile (5 ml)
6. customthe solution was dried by freeze
7. customdrying
8. dissolutionthe solid was then dissolved in methylene chloride (10 ml)
9. additionSolid NaHCO3 (approx. 500 mg) was added to this solution
10. stirringthe mixture was stirred for 1 hour
11. filtrationThe mixture was then filtered
12. concentrationthe filtrate was concentrated in vacuo

ORDレコード

ord-e890b0c653564deb88a7841a4788079a

出典データセット

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08268814B2