; 1H NMR
(CDCl3) δ: 0.89–0.95 (t, 3H, CH2 CH 3 J = 7.5 Hz); 1.51–1.60 (m, 2H, –CH2 CH 2 CH3); 2.33–2.38 (m, 2H, –CH3CH2 CH 2 –); 2.52–2.56 (m, 4H CH2 CH 2 N); 2.75–2.78 (t, 2H, CH2-thiazole J = 5.7 Hz); 3.45–3.49 (m, 4H, –CH2 CH 2 N); 3.84–3.87 (t, 2H CH 2 OH, J = 5.7 Hz) 4.01 (s* br, H, OH–) 6.20 (s, 1H, H thiazole); TLC (methylen chloride:methanol 10:1) R f = 0.27. Elemental analysis for dihydrobromide C12H21N3OSx2HBr (M = 417,22) C H N Calculated 34.54 % 5.56 % 10.07 % Found 34.30 % 5.52 % 10.07 % mpdihydrobromide 244–246 °C The synthesis of 1-[2-thiazol-4-yl-(2-mesyloxyethyl)]-4-n-propylpiperazine (9) To a cooled solution of click here the 1-[2-thiazol-4-yl-(2-hydroxyethyl)]-4-n-propylpiperazine find more (8) (0.009 mol) in 10 mL of dry pyridine, while stirring, methanesulfonyl Sotrastaurin chemical structure chloride (0.009 mol) was added dropwise. The mixture was stirred at room temperature for 0.5 h. Then, reaction mixture was poured out in ice-cold water (40 mL) and extracted with ethyl ether (3 × 50 mL). The combined organic extracts were dried (Na2SO4),
filtered and evaporated to give compound 9 as a sticky yellow oil. The crude compound 9 was used in the next step without further purification. 9. C13H23N3O3S2 (M = 333); yield 58.1 %; 1H NMR (CDCl3) δ: 0.90–0.95 (t, 3H, CH2 CH 3 J = 7.4 Hz); 1.48–1.60 (m, 2H, –CH2 CH 2 CH3); 2.33–2.38 (m, 2H, –CH3CH2 CH 2 –); 2.52–2.56 (m, 4H CH2 CH 2 N); 2.92 (s, 3H, CH 3 SO3) 2.96–3.02 (t, 2H, CH2-thiazole J = 6.6 Hz); 3.45–3.48 (m, 4H, –CH2 CH 2 N); 4.49–4.52 (t, 2H
CH 3 SO3 CH 2, J = 6.6 Hz) 6,29 (s, 1H, H thiazole); TLC (methylen chloride:methanol 10:1) Rf = 0.44. The synthesis of 1-[2-thiazol-4-yl-(2-methylaminoethyl)]-4-n-propylpiperazine (10) The crude 1-[2-thiazol-4-yl-(2-mesyloxyethyl)]-4-n-propylpiperazine 9 (0.008 mol) was dissolved in 30 mL of 40 % solution methylamine in methanol. The mixture was stirred at room temperature for 24 h. Then, organic solvent was evaporated, and residue was dissolved in DME (40 mL), alkalized with solid NaHCO3 (0.001 mol) and stirred for 1 h. The mixture was filtered and DME was evaporated to give compound (-)-p-Bromotetramisole Oxalate 2 as a yellowish sticky oil. The free base was dissolved in small amount of n-propanol and treated with methanolic HBr. The treehydrobromide crystallized as white solid. 2. C13H24N4S (M = 268); yield 68.9 %; 1H NMR (CDCl3) δ: 0.90–0.95 (t, 3H, CH2 CH 3 J = 7.5 Hz); 1.50–1.60 (m, 2H, –CH 2 CH3); 2.01 (s* br, 1H, NH); 2.32–2.37 (m, 2H, –CH3CH2 CH 2 –); 2.45 (s, 3H –CH 3); 2.52–2.56; (m, 4H CH2 CH 2 N); 2.73–2.77 (t, 2H, CH 2 -thiazole, J = 6.6 Hz); 2.86–2.91 (t, 2H, CH 2N J = 6.6 Hz) 3.45–3.48 (m, 4H, CH2 CH 2 N); 6.19 (s, 1H, H thiazole); TLC (chloroform metanol concentrated ammonium hydroxide 60:10:1) Rf = 0.10. Elemental analysis for treehydrobromide C13H27N4 Br3S (511,20) C H N Calculated 30.54 % 5.32 % 10.96 % Found 30.61 % 5.23 % 10.