[H-].[Na+].Br[CH2:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[CH3:22])(=[O:14])=[O:13])[S:9][CH:10]=1.OC1C=NC=CC=1.Cl>O1CCCC1>[Cl:21][C:17]1[C:16]([CH3:22])=[C:15]([S:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([CH:5]=[CH2:4])[N:7]=2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1Sodium hydride (95% dry, 32 mg, 1.27 mmol) was added to a stirred solution of the product from Step 3 (240 mg, 0.61 mmol) and 3-hydroxypyridine (63 mg, 0.67 mmol) in tetrahydrofuran (10 mL) at 0° C. After 2 h at reflux temperature the reaction was neutralized by adding 2 M HCl and the product mixture was extracted with dichloromethane. The organic phase was dried (Na2SO4) and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel gradient eluting with 2-5% acetone in dichloromethane giving the title compound as a solid (33 mg, 17%). MS (Ionspray, [M+H]+) m/z 314; Anal. Calcd. (found) for C12H11ClN2O2S2: C 45.8 (45.0) % H 3.5 (3.9) %N 8.9(9.1) %.
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