Potassium Carbonate → N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]-N'-methylurea

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]-N′-methylurea (i.e. the product of Step A) (0.30 g, 1.1 mmol) in dioxane (3.0 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.07 mL, 0.45 mmol) followed by copper(I) iodide (0.085 g, 0.45 mmol), potassium carbonate (0.94 g, 6.8 mmol) and 3,4-dihydro-6-iodo-2H-1-benzopyran (0.44 g, 1.7 mmol; prepared as cited in Step E of Synthesis Example 4). The reaction mixture was heated to 110° C. for 20 h and then cooled to ambient temperature. The solvent was evaporated, and the residue was taken up in chloroform, washed with water and brine, and then dried (Na2SO4) and concentrated. The crude residue was purified by preparative TLC (1.5% methanol in dichloromethane as eluant) to provide the title product a compound of the present invention, as a solid (0.036 g).

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