4-Toluenesulfonyl chloride → HCID 11988575, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-(4-hydroxy-2,2-dimethyl-4-pyridin-3-yl-butylamino)-3-methyl-benzonitrile (570 mg, 1.66 mmol) in pyridine (2.3 mL) add tosyl chloride (950 mg, 4.98 mmol) in pyridine (1.2 mL) at room temperature. Heat the reaction mixture at 100° C. for 24 h, add additional tosyl chloride (950 mg), and heat for 24 h at 100° C. Cool to room temperature and concentrate under vacuum. Dissolve the residue in ethyl acetate and wash with water. Dry the organic layer over anhydrous sodium sulfate and concentrate to obtain a brown oil. Purify the oil by silica gel chromatography and preparative HPLC to obtain the title compound. Mass spectrum (m/e): 326 (M+H).

Provenance & Evidence