1-Pyrrolidineethanamine → 3-Amino-5-chloro-4-methyl-6-[(2-pyrrolidin-1-yl-ethylcarbamoyl)-methoxy]-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Participants

Reaction Steps

To a solution of (3-amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid (0.300 g, 0.843 mmol) in a 1:1 mixture of THF:DMF (2.0 ml each) are added 1-hydroxybenzotriazole hydrate (0.148 g, 1.096 mmol), N,N-diisopropylethylamine (0.163 g, 1.265 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.242 g, 1.265 mmol), and 1-(2-aminoethyl)pyrrolidine (0.289 g, 2.529 mmol). The resulting solution is stirred at room temperature for 16 hours. The reaction is quenched by the addition of water (25 ml). A yellow precipitate formed. The mixture is cooled to 0° C. and stirred for 10 minutes, then filtered. The collected solid is dried in the vacuum oven for 3 hours at 60° C. This affords the title compound as a yellow solid (0.069 g, 18%). Mass (m/z): 452.2 (M++1), 450.2 (M+−1).

Provenance & Evidence