m-Chloroperbenzoic acid → HCID 69309550, compound

Participants

Reaction Steps

4-(2-Methylsulfanyl-ethoxymethyl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H indole (196 mg, 0.36 mmol) was dissolved in DCM, cooled on an ice bath, and MCPBA (635 mg, 2.83 mmol) was added and the mixture was stirred at RT overnight. The mixture was then diluted with DCM, washed with 5% NaHCO3, dried over sodium sulfate, filtered, concentrated in vacuo, and the residue dissolved in NMP and added to a suspension of N-(4-amino-cyclohexyl)-N-methyl-methanesulfonamide (409 mg, 1.98 mmol), 0.39 mL DIEA (2.27 mmol) and molecular sieves (previously stirred at RT for 1 h). The mixture was stirred at 120° C. for 1 h, cooled to RT, the mixture decanted into water, stirred for 30 min, filtered, and the precipitate purified by flash chromatography, eluting with DCM:MeOH 97:3. The product was then stirred in ether, filtered, and the solvent removed in vacuo overnight to yield N-methyl-N-(4-{4-[4-(2-methylsulfanyl-ethoxymethyl)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide (47 mg).

Provenance & Evidence