Seven novel [5,6]. 2H), 2.47 (s, 3H), 1.17 (t, = 7.2 Hz, 3H). EI-MS (2a): White solid, Rabbit polyclonal to Cytokeratin5 m.p. 220C221 C. 1H-NMR (300 MHz, CDCl3) = 8.4 Hz, 1H), 8.14 (s, 1H), 7.93 (d, = 7.5 Hz, 2H), 7.73 (s, 1H), 7.58C7.63 (m, 1H), 7.48C7.53 (m, 2H), 7.15 (d, = 8.1 Hz, 1H), 2.56 (s, 3H, COCH3), 2.47 (s, 3H, CH3). ESI-TRAP-MS (2b): White solid, m.p. 118C120 C. 1H-NMR (400 MHz, CDCl3) = 8.4 Hz, 1H), 8.14 (s, 1H), 7.84 (d, = 8.0 Hz, 2H), 7.74 (s, 1H), 7.30 (d, = 8.0 Hz, 2H), 7.15 (d, = 8.0 Hz, 1H), 2.66 (q, = 7.6 Hz, 2H, CH2CH3), 2.55 (s, 3H, COCH3), Dabigatran 2.48 (s, 3H, CH3), 1.18 (t, = 8.0 Hz, 3H, CH2CH3). EI-MS and purifed by silica gel column chromatography to provide the pure substances 4aCf. The constructions of the substances were well seen as a 1H-NMR, 13C-NMR, m.p., and MS. (4a): Yellow solid, produce 73%, m.p. 132C134 C. 1H-NMR (400 Dabigatran MHz, CDCl3) = 8.4 Hz, 1H), 8.18 (s, 1H), 7.95C7.97 (m, 2H), 7.91 (s, 1H), 7.58C7.60 (m, 1H), 7.47C7.51 (m, 2H), 7.31 (d, = 8.4 Hz, 1H), 3.59 (s, 2H), 2.57 (s, 3H), 2.34 (s, 4H), 1.55C1.60 (m, 4H), 1.43C1.44 (m, 2H). Dabigatran 13C-NMR (125 MHz, CDCl3) (%): 397 ([M+H]+, 100). HRMS (ESI): Calcd for C22H25N2O3S ([M+H]+), 397.1580; found out, 397.1571. (4b): White colored solid, produce 66%, m.p. 174C176 C. 1H-NMR (500 MHz, CDCl3) = 8.0 Hz, 1H), 8.19 (s, 1H), 7.94C7.96 (m, 2H), 7.90 (s, 1H), 7.62 (t, = 7.5 Hz, 1H), 7.48C7.51 (m, 2H), 7.33 (dd, = 8.0 Hz, 1.0 Hz, 1H), 3.71 (t, = 4.5 Hz, 4H), 3.61 (s, 2H), 2.57 (s, 3H), 2.41 (t, = 4.0 Hz, 4H). 13C-NMR (125 MHz, CDCl3) (%): 399 ([M+H]+, 100). HRMS (ESI): Calcd for C21H23N2O4S ([M+H]+), 399.1373; found out, 399.1361. (4c): Yellowish solid, produce 57%, m.p. 124C126 C. 1H-NMR (500 MHz, CDCl3) = 8.5 Hz, 1H), 8.18 (s, 1H), 7.95C7.97 (m, 2H), 7.91 (s, 1H), 7.58C7.61 (m, 1H), 7.47C7.50 (m, 2H), 7.33C7.35 (m, 1H), 3.75 (s, 2H), 2.56 (s, 3H), 2.49 (s, 4H), 1.78C1.80 (m, 4H). 13C-NMR (125 MHz, CDCl3) (%): 383 ([M+H]+, 100). HRMS (ESI): Calcd for C21H23N2O3S ([M+H]+), 383.1424; found out, 383.1417. (4d): Tan water, produce 49%. 1H-NMR (500 MHz, CDCl3) = 8.0 Hz, 2H), 7.57C7.60 (m, 1H), 7.46C7.49 (m, 2H), 7.32 (d, = 8.0 Hz, 1H), 3.74 (s, 2H), 2.99C3.04 (m, 2H), 2.56 (s, 3H), 1.03 (d, = 6.5 Hz, 12H). 13C-NMR (125 MHz, CDCl3) (%): 413 ([M+H]+, 100). HRMS (ESI): Calcd for C23H29N2O3S ([M+H]+), 413.1893; found out, 413.1890. (4e): Yellowish liquid, produce 51%. 1H-NMR (500 MHz, CDCl3) = 8.5 Hz, 1H), 8.18 (s, 1H), 7.95C7.97 (m, 2H), 7.90 (s, 1H), 7.59C7.62 (m, 1H), 7.48C7.51 (m, 2H), 7.31C7.33 (m, 1H), 3.91 (s, 2H), 2.75 (s, 1H), 2.58C2.61 (m, 2H), 2.56 (s, 3H), 1.48C1.51 (m, 2H), 1.32C1.36 (m, 2H), 0.89C0.92 (m, 3H). 13C-NMR (125 MHz, CDCl3) (%): 385 ([M+H]+, 100). HRMS (ESI): Calcd for C21H25N2O3S ([M+H]+), 385.1580; found out, 385.1572. (4f): White colored solid, produce 37%, m.p. 108C110 C. 1H-NMR (500 MHz, CDCl3) = 8.5 Hz, 1H), 8.19 (s, 1H), 7.92 (s, 1H), 7.87 (d, = 8.0 Hz, 2H), 7.29C7.33 (m, 3H), 3.71 (s, 4H), 3.62 (s, 2H), 2.68(q, = 7.5 Hz, 2H), 2.56 (s, 3H), 2.42 (s, 4H), 1.21 (t, = 7.5 Hz, 3H). 13C-NMR (125 MHz, CDCl3) (%): 427 ([M+H]+, 100). HRMS (ESI): Calcd for C23H27N2O4S ([M+H]+), 427.1686; found out, 427.1677. 3.3. General Process of the formation of 6 First of all, intramolecular cyclization of benzoylhydrazine with carbon disulfide and potassium hydroxide in the current presence of ethanol led to 5-phenyl-1,3,4-oxadiazole-2-thiol (5) [10]. Subsequently, an assortment of Dabigatran 5 (0.5 mmol), 3b (0.6 mmol) and K2CO3 (1 mmol) in acetone (5 mL) was reacted at reflux, as well as the response.