Water → (2S)-(2-Methoxymethyl-pyrrolidin-1-yl)-[7-(2-methyl-quinolin-6ylamino)-thieno[3,2-b]pyridin-2-yl]-methanone

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Reaction Conditions

Reaction Steps

Cesium Carbonate (117 mg, 0.36 mmol) was added to a solution of (7-chloro-thieno[3,2-b]pyridin-2-yl)-(2-hydroxymethyl-pyrrolidin-1-yl)-methanone 1(56 mg, 0.18 mmol) in DMF (4 mL). The reaction mixture was heated to 85° C. for 1.5 hours with stirring. After cooling to room temperature, 2-methyl-quinolin-6-ylamine (57 mg, 0.36 mmol) was added to the reaction mixture, and the resulting mixture was heated to 90° C. for 48 hours. The reaction mixture was treated with water and extracted with EtOAc (3×15 mL). The combined organic extracts were was dried over sodium sulfate, and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel with CH2Cl2/MeOH (95/5) afforded the title compound as a white solid. MS: 435 (MH+); HPLC Rf: 5.35 min; HPLC purity: 97%.

Provenance & Evidence