Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-2-(phenylsulfanyl)-1,3-thiazole-5-carboxamide Fumarate

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Reaction Steps

HATU (0.493 g, 1.30 mmol, 1 eq) is added to a solution of 2-phenylsulfanyl-thiazole-5-carboxylic acid (0.307 g, 1.30 mmol, 1 eq), (R)-(+)-3-aminoquinuclidine dihydrochloride (0.258 g, 1.30 mmol, 1 eq), and DIEA (0.677 mL, 3.89 mmol, 3 eq) in DMF (9.8 mL), the flask containing which was in an ice bath. The reaction is stirred overnight. CH2Cl2 is added, and the mixture is washed with water three times. The organic layer is dried over MgSO4, and the solvent removed in vacuo. The product is purified using a Biotage Flash 40M column (1% NH4OH/9% MeOH/90%CH2Cl2), affording a clear oil. The fumaric acid salt of the product is made, and recrystallized from MeOH and ether to give the product as a white crystalline solid (0.408 g, 72%). MS (ESI) for C17H19N3OS2 m/z 346.1 (M+H)+.

Provenance & Evidence