N,N'-Dimethylethylenediamine → HCID 24803251, compound

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Reaction Steps

Combine 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (1.8 g, 6.88 mmol), N-(4-bromo-2-methoxy-phenyl)-2-pyrrolidin-1-yl-acetamide (2.58 g, 8.25 mmol), Cs2CO3 (4.48 g, 13.8 mmol), 1,4-dioxane (69 mL), and CuI (0.520 g, 2.75 mmol). Purge the mixture with nitrogen for 10 min. Add sym-dimethylethylene diamine (0.49 g, 5.50 mmol) and heat the mixture at 100° C. overnight. Cool the mixture to RT, dilute with CH2Cl2, and wash twice with a solution of 5% NH4OH/H2O (2×). Dry the organic layer over Na2SO4, filter, and concentrate. Filter the crude with H2O and Et2O. Purify the crude material by chromatography using a gradient of 20-50% acetone in hexane. Prepare the HCl salt by dissolving the solid with CH2Cl2. Add 1 eq of 1 M HCl/ether, allow the solution to stir for 15 min, and concentrate to give 1.95 g (53%) of the title compound. LC-ES/MS m/z (35Cl) 494.0 [M+H]+.

Provenance & Evidence