[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:16]([O-:19])(O)=O.[Na+].C(Cl)(Cl)=O.C[CH2:26][N:27](CC)[CH2:28]C.Cl.CNC>C(Cl)Cl.C1(C)C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([NH:1][C:16](=[O:19])[N:27]([CH3:28])[CH3:26])[CH:3]=[CH:4][C:5]=1[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:8]To 15C (67 mg, 0.30 mmol) in methylene chloride (2 mL) at 0° C. was added NaHCO3 (252 mg, 3 mmol) followed by a ca. 20% phosgene solution in toluene (0.3 mL). After stirring at that temperature for 2 h, the reaction was concentrated and diluted with methylene chloride (3 mL). To this solution was added Et3N (130 mg, 1.28 mmol) followed by dimethylamine hydrochloride (43 mg, 0.53 mmol) and the reaction was stirred overnight. The solution was loaded onto a silica gel column and purified via silica gel chromatography (0-80% ethyl acetate/hexane) to provide 16A (44 mg, 50%) and recovered starting material (15C) (20 mg). 16A: LC-MS: 296.02 (M+H)+.
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