[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[N:19]=[C:18](Cl)[S:17][N:16]=1.C(N(CC)CC)C>CS(C)=O.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:18]1[S:17][N:16]=[C:15]([Cl:14])[N:19]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2]
(3-Methylamino-propyl)-carbamic acid tert-butyl ester (7.00 g, 36.8 mmol) and 3,5-dichloro-[1,2,4]thiadiazole (4.75 g, 30.7 mmol) were dissolved in DMSO (150 mL). Finally, triethylamine (3 mL) was added and the reaction mixture was stirred at room temperature for 24 h. After this period, brine (100 mL) was poured into the reaction vessel and the mixture was transferred to a separatory funnel. The resulting layer was extracted with DCM (3×300 mL). The DCM layer was then dried over anhydrous Na2SO4. The crude product was purified using flash silica chromatography (DCM to 9:1 DCM/MeOH) to afford 6.5 g (69%) of {3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 307.40.
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