Pyridine → HCID 58713644, compound

Reaction equation

[C:1]([O:5][C:6]([C:8]1[C:12]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[CH:15][C:11]=2[NH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[C:12]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[CH:15][C:11]=2[N:10]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Procedure

To a solution of the pyrazole intermediate from step A (275 mg, 1.1 mmol) above in CH2Cl2 (5 mL) was added pyridine (178 μL, 2.2 mmol) and p-toluene sulfonyl chloride (230 mg, 1.21 mmol). After stirring the resulting reaction mixture at room temperature for 3 hours it was diluted with CH2Cl2, washed with 1N HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2) using 10% ethyl acetate-hexanes.