Benzenesulfonyl chloride → N-[2-({[(1R)-1-Phenylethyl]amino}methyl)-3,4-dihydro-2H-chromen-7-yl]-2,1,3-benzoxadiazole-4-sulfonamide

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A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (28.6 mg, 160 μmol) in pyridine is treated with 2,1,3-benzoxadiazole-4-sulfonyl chloride (39 mg, 180 μmol) at ambient temperatures, stirred for 1 h, treated with phenylsulfonyl chloride (23 μL, 180 μmol) stirred for an additional hour at ambient temperatures, treated with (1R)-1-phenyl-1-ethanamine (1.6 mmol, 206 μL), heated to 100° C. for 2 h, cooled to room temperature, diluted with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by reverse phase preparative HPLC to give the title product, M+H 465, retention time 3.89 min.

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