9355(6)?, �� = 95.1220(ten)��, �� = 92.6030 (10)��, �� = 111.2940(ten)��, ��calcd = one.370g/cm3, Mo-radiation (�� = 0.71073?), T = one hundred(two)K, reflections collected = 19486, independent reflections = 6602 (Rint. = 0.0316), absorption coefficient �� = 0.786mm?one, 433 variables converged at R1 = two.96%, wR2 = 7.70% for all information, with BTK signaling pathway inhibitor intensity I > 2��(I), the ultimate big difference map was 0.513 and ?0.437e??3.2.2. kinase inhibitor RVX-208 Synthesis of one,2,3-Triazoles Performed below AgCl CatalysisGeneral Process. AgCl (0.005g, 0.035mmol) was extra to a stirred alternative containing the corresponding alkyne (1.0mmol) as well as the proper azide (one.1mmol) in H2O (3mL) and acetone (1mL). The resulting response mixture was stirred at room temperature for 24h. The acetone was eliminated in vacuo, and CH2Cl2 (20mL) was extra.
The organic layer was separated, along with the aqueous phase was extracted with CH2Cl2(three �� 10mL). The organic phases have been joined, dried over Na2SO4 and filtered. The solvent was removed under reduced strain plus the ultimate merchandise was purified by crystallization.two.three. Synthesis of 1,2,3-Triazoles Performed under Silver Complex CatalysisGeneral Method. The silver complicated 14 (0.0005mmol) was additional to a stirred alternative containing the corresponding alkyne (1.0mmol) as well as the ideal azide (1.05mmol) in THF (4mL). The resulting reaction mixture was stirred at space temperature for 24h. The acetone was eliminated in vacuo, and CH2Cl2 (20mL) was added. The natural layer was separated, plus the aqueousSRT1720 phase was extracted with CH2Cl2(3 �� 10mL). The natural phases had been joined, dried over Na2SO4, and filtered.
The solvent was eliminated under diminished strain, as well as the ultimate product was purified by crystallization.2.4. 1-Benzyl-4-phenyl-1,2,3-triazole (three) Phenylacetylene and benzyl azide afforded 1-benzyl-4-phenyl-1,2,3-triazole as white sound. Yields: 150.8mg (64%, beneath AgCl catalysis) and 181.1mg (77%, below silver complicated catalysis). m.p. 132��C (lit. 130-130.9��C) . IR (ATR) ��max /cm?one: 3250, 2850, 1650, and 1600. 1H NMR (500MHz, CDCl3) ��/ppm: 5.59 (s, 2H), seven.33�C7.39 (m, 1H), 7.41-7.41 (m, 4H), seven.68�C7.82 (m, 2H), and 7.68 (s, 1H). 13C NMR (125MHz, CDCl3) ��/ppm: 54.two (CH2), 119.five (CH), 125.six (2 �� CH), 127.9 (two �� CH), 128.one (CH), 128.seven (CH), 128.eight (2 �� CH), 129.1 (2 �� CH), 130.5(CH), 134.six (C), and 148.two (C).
MS (EI+) m/z (%): 235[M]+ (21), 206 [M�CHN2]+ (74), 116 [M�CC6H5N3]+ (100), and 91 [C6H5CH2]+ (94).
2.five. (1-Benzyl-1,2,3-triazol-4-yl)-methanol (4) Propargyl alcohol and benzyl azide afforded (1-benzyl-1,2,3-triazol-4-yl)-methanol as white strong. Yields: 109.7mg (58%, below AgCl catalysis) and 120.3mg (63%, below silver complicated catalysis). m.p. 77.8��C (lit. 76-77��C) . IR (ATR) ��max /cm?1: 3330, 2850, and 1600. 1H NMR (500MHz, CDCl3) ��/ppm: three.36 (s, 1H), four.51 (s, 2H), 5.57 (s, 2H), 7.30�C7.37 (m, 5H), and eight.00 (s, 1H).