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

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Reaction Steps

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]+

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