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From 4-chlorothieno[3,2-= 6

From 4-chlorothieno[3,2-= 6.3 Hz, 6H), 2.79C2.85 (m, 2H), 3.61C3.73 (m, 2H), 4.60 (d, = 13.0 Hz, 2H), 7.39 (d, = 5.6 Hz, 1H), 7.69 (d, = 5.6 Hz, 1H), 8.54 (s, 1H) ppm. 148.2 (C), 162.3 (C) ppm. (5). From 4-chloro-2-methylimidazo[1,5-(6). From 4-chloro-2-methylimidazo[1,5-= 7.9 Hz, 1H), 7.20 (t, = 7.6 Hz, 1H), 7.52 (t, = 7.6 Hz, 1H), 7.68 (d, = 7.8 Hz, 1H), 8.25 (s, 1H), 10.30 (s, 1H) ppm.13C-NMR (100.6 MHz, CDCl3) 19.0 (CH), 90.6 (CH), 92.4 (C), 114.9 (C), 122.1 (CH), 123.4 (CH), 126.8 (C), 126.9 (CH), 126.9 (C), 127.5 (CH), 132.7 (CH), 139.2 (C), 143.5 (C), 146.2 PTC-209 HBr (C), 146.4 (C) ppm. 19F-NMR (376 MHz, CDCl3) ?61.9 ppm. HRMS: calcd for C15H11F3N5 [M + H]+ 318.0961, found 318.0964. (7) [75]. From 7-chloro-5-methyl-[1,2,4]triazolo[1,5-(8) [76]. From 7-chloro-5-methyl-[1,2,4]triazolo[1,5-(9). From 7-chloro-5-methyl-[1,2,4]triazolo[1,5-= 6.3 Hz, 6H), 2.56 (s, 3H), 2.67C2.76 (m, 2H), 3.84C3.95 (m, 2H), 4.35 (d, = 11.6 Hz, 2H), 6.11 (s, 1H), 8.27 (s, 1H) ppm. 13C-NMR (63 MHz, CDCl3) 18.8 (2xCH), 25.2 (CH), 53.1 (2xCH), 71.2 (2xCH), 94.4 (CH), 149.9 (C), PTC-209 HBr 154.2 (CH), 157.2 (C), 164.9 (C) ppm. CAS: 950030-11-2; Distributor Name: Aurora Great Chemical substances Ltd., A-8010 Graz, Austria. (10). (69 mg, 88%), m.p 130C132 C. 1H-NMR (400 MHz, CDCl3) 0.94 (t, = 7.4 Hz, 6H), 1.33C1.39 (m, 4H), 1.66 (s, 2H), 2.50 (s, 3H), 3.64 (s, 2H), 3.74C3.78 (m, 4H), 5.90 (s, 1H), 8.18 (s, 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 13.8 (2xCH), 20.0 (2xCH), 25.1 (CH), 30.1 (CH), 51.6 (2xCH), 70.5 (CH), 92.3 (CH), 149.1 (C), 153.7 (CH), 157.9 (C), 163.7 (C) ppm. HRMS: calcd for C14H24N5 DDPAC [M + H]+ 262.2026, found 262.2027. (11). From 8-chloro-[1,2,4]triazolo[4,3-= 4.5 Hz, 1H), 7.36 (d, = 4.5 Hz, 1H), 8.68 (s, PTC-209 HBr 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 24.7 (CH), 26.2 (2xCH), 47.4 (2xCH), 106.0 (CH), 129.8 (CH), 136.6 (CH), 140.5 (C), 147.9 (C) ppm. CAS:1878022-44-6; Distributor Name: Sigma-Aldrich, F 38297 Saint-Quentin Fallavier, France. (12). From 8-chloro-[1,2,4]-triazolo[4,3-= 6.3 Hz, 6H), 2.73C2.81 (m, 2H), 3.57C3.59 (m, 1H), 3.66C3.73 (m, 2H), 5.33 (s, 1H), 7.27 (d, = 4.5 Hz, 1H), 7.41 (d, = 4.5 Hz, 1H), 8.71 (s, 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 18.8 (2xCH), 71.9 (2xCH), 106.8 (CH), 129.5 (CH), 136.7 (CH), 140.3 (C), 147.7 (2xCH), 160.6 (C) ppm. CAS: 2127319-44-0; Distributor Name: Aurora Great Chemical substances Ltd., A-8010 Graz, Austria. (13). From 8-chloro-[1,2,4]triazolo[4,3-= 7.4 Hz, 6H), 1.34C1.41 (m, 4H), 1.67 (t, = 7.7 Hz, 4H), 4.00 (s, 4H), 7.27 (d, = 4.5 Hz, 1H), 7.32 (d, = 4.5 Hz, 1H), 8.67 (s, 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 14.0 (3xCH), 20.1 (2xCH), 30.4 (CH), 49.5 (2xCH), 105.3 (CH), 130.1 (CH), 136.5 (CH), 140.4 (C), 148.0 (C) ppm. HRMS: calcd for C13H22N5 [M + H]+ 248.1870, found 248.1871. (14). From 8-chloro-[1,2,4]triazolo-[4,3-= 7.6 Hz, 1H), 7.44 (d, = 4.7 Hz, 1H), 7.60 (d, = 4.7 Hz, 1H), 7.63 (t, = 7.9 Hz, 1H), 7.71 (d, = 7.8 Hz, 1H), 8.39 (s, 1H), 8.53 (d, = 8.3 Hz, 1H), 8.82 (s, 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 109.2 (CH), 121.0 (C), 124.3 (2xCH), 125.4 (C), 126.6 (CH), 129.2 (CH), 132.7 (CH), 135.6 (C), 137.4 (CH), 139.2 (C), 145.4 (C) ppm. 19F-NMR (376 MHz, CDCl3) ?60.7 ppm. HRMS: calcd for C12H9F3N5 [M + H]+ 280.0805, found 280.0805. (15). From 4-chlorofuro[3,2-= 2.2 Hz, 1H), 7.68 (d, = 2.2 Hz, 1H), 8.41 (s, 1H) ppm.13C-NMR (100.6 MHz, CDCl3) 24.7 (CH),26.0 (2xCH), 46.3 (2xCH), 107.8 (CH), 134.4 (C), 147.1 (CH), 148.4 (C), 151.0 (C), 153.4 (CH) ppm. HRMS: calcd forC11H14N3O [M + H]+ 204.1131, found 204.1135. (16). From 4-chlorothieno[3,2-= 5.6 Hz, 1H), 7.62 (d, = 5.6 Hz, 1H), 8.49 (s, 1H) ppm. 13C-NMR (100.6 MHz, CDCl3) 24.7 (CH), 26.1 (2xCH), 47.4 (2xCH), 114.2 (C), 125.1 (CH), 131.1 (CH), 154.2 (CH), 157.8 (C), 161.0 (C) ppm. CAS: 679394-37-7; Distributor Name: SIA Enamine, LV-1035 Riga, Latvia. (17). From 4-chlorofuro[3,2-= 2.2 Hz, 1H), 7.72 (d, PTC-209 HBr = 2.2 Hz, 1H), 8.46 (s, 1H) ppm. 13C-NMR (101 MHz, CDCl3) 45.5 (2xCH), 66.84 (2xCH), 107.96 (CH), 134.3 (C), 147.6 (CH), 148.43 (C), 151.5 (C), 153.3 (CH) ppm. HRMS: calcd for C10H12N3O2 [M + H]+ 206.0924, 206.0926 found. (18) [77]. From.