General Papers
ARKIVOC 2016 (v) 318-326
d6, δ, ppm): 8.94, 23.04, 109.18, 119.12, 124.07, 132.12, 150.48, 162,54, 173.70; Anal. calcd. for C16H16N6O: C, 62.32, H, 5.23, N, 27.26: Found: C, 62.45, H, 5.09, N, 27.39 %. Synthesis of 4-[4,6-Bis(cyclopropylamino)-1,3,5-triazin-2-yloxy]-N'-hydroxybenzamidine (8). Solution of hydroxylamine hydrochloride (0.69 g, 0.01 mol) in methanol (10 mL) was added to potassium hydroxide (0.56 g, 0.01 mol) in methanol (10 mL) and stirred at room temperature for 20 min; KCl precipitated out and was removed by filtration. The nitrile 7 (3.08 g, 0.01 mol) was added to the filtrate obtained, and the solution was stirred overnight at 40 oC, and then concentrated. The solid formed was triturated with water and dried. Further purification of the product obtained was done on silica column (eluent: petroleum ether/ EtOAc, 9:1). White solid (3.11 g, 72%), mp 181-183 oC. IR (KBr) νmax/ cm-1: 3510 cm-1 (broad OH str.), 33303250 cm-1 (NH2 str.), 1335 cm-1 (C-O-C), 2900 (C-H, Ar-H str.), 1580 (NH bending), 811 (striazine); 1H NMR (400 MHz, DMSO-d6, δ, ppm); 0.40 – 0.56 (4H, m, CH2, cyclopropyl), 1.17 (2H, s, NH2), 2.40 (1H, m, CH, cyclopropyl), 4.59 (1H, m, NH, cyclopropylamino), 5.54 ( 1H, s, OH), 7.23 (2H, d, J 7.5 Hz, phenoxyl), 7.27 (2H, J 7.5 Hz, phenoxyl); 13C NMR (100 MHz, DMSO-d6, δ, ppm): 8.94, 23.04, 124.03, 126.64, 127.55, 148.29, 151.01, 162.54, 173.70; Anal. calcd. for C16H19N7O2: C, 56.29, H, 5.61, N, 28.72: Found: C, 56.15, H, 5.34, N, 28.93 %. Synthesis of 6-[4-(5-Methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N2,N4-dicyclopropyl-1,3,5-triazine2,4-diamine (9). Compound 8 (1.70 g, 0.005mol) was refluxed in acetyl chloride (15 ml) for 6 h. The unreacted acetyl chloride was evaporated in a rotary evaporator and the residue obtained was recrystallized from ethanol. White solid (1.2 g, 71%), mp 116-118 oC. IR (KBr) νmax/ cm-1: 3360 cm-1 (NH str.), 1352 cm-1 (CO-C), 2855 (C-H, Ar-H str.), 1587 (NH bending), 1470 (C-H bending, CH3), 1090 (C-O), 827 (striazine); 1H NMR (400 MHz, DMSO-d6, δ, ppm); 0.42 – 0.56 (4H, m, CH2, cyclopropyl), 2.20 (3H, s, CH3, oxadiazole), 2.40 (1H, m, CH, cyclopropyl), 3.44 (1H, m, NH, cyclopropylamino), 7.03 (2H, d, J 7.5 Hz, phenoxyl), 7.47 (2H, m, J 7.5 Hz, phenoxyl); 13C NMR (100 MHz, DMSOd6, δ, ppm): 8.94, 13.73, 23.04, 121.94, 126.30, 129.15, 152.92, 162.54, 165.68, 173.45, 173.70; Anal. calcd. for C18H19N7O2: C, 59.17, H, 5.24, N, 28.83: Found: C, 59.27, H, 5.33, N, 26.75 %.
References 1. Shah, D. R.; Modh, R. P.; Chikhalia, K. H. Future. Med. Chem. 2014, 6(4), 463-477. http://dx.doi.org/10.4155/fmc.13.212 2. Shanmugam, M.; Narayanan, K.; Chidambaranathan, V.; Kabilan, S. Spectrochim Acta A Mol Biomol Spectrosc. 2013, 105, 383-390. http://dx.doi.org/10.1016/j.saa.2012.12.046 3. Singh, U. P.; Bhat, H. R.; Gahtori, P. J. Med. Mycol. 2012, 22(2), 134-141. http://dx.doi.org/10.1016/j.mycmed.2011.12.073 4. Klenke, B.; Stewart, M.; Barret, M. P.; Burn, R.; Gilbert, I. H. J. Med. Chem. 2001, 44, 34403452.
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