[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)=[O:8].[H-].[Na+].Cl[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]([CH3:15])=[CH:13][N:14]\1[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)=[O:8]To a solution of Example 340A (0.15 g, 0.53 mmol) in 5 mL DMF was added sodium hydride (0.016 g, 0.67 mmol, 95%). After the solution was allowed to stir at ambient temperature for 30 min, 2-(chloromethyl)furan (0.08 g, 0.67 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.075 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.26 (d, J=1.36 Hz, 3H) 3.80 (s, 3H) 5.18 (s, 2H) 6.54 (s, 1H) 7.12 (d, J=8.81 Hz, 1H) 7.29 (d, J=1.36 Hz, 1H) 7.46 (dd, J=8.81, 2.71 Hz, 1H) 7.64 (t, J=1.70 Hz, 1H) 7.67-7.76 (m, 2H). m/z 363.0 (M+H)+.
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