[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[C:11]([C:15]3([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>ClCCCl>[C:33]1([O:32][C:30](=[O:31])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH:10]=3)=[CH:4][CH:3]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1A mixture of 4-{3-[(4-aminophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carbonitrile (2.50 g, 8.06 mmol) (example 4) in 1,2-dichloroethane (20 mL) and pyridine (0.95 g, 12.097 mmol) was cooled to 0° C. Phenyl chloroformate (1.89 g, 12.097 mmol) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for about 1 hour. The solvent was evaporated under vacuum, toluene was added to remove traces of pyridine, then hexane was added and the solid so obtained was filtered and dried. Yield:4.30 g.
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