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2.6. 4-(1-Benzyl-1,two,3-triazol-4-ylmethoxy)-benzoic Lumacaftor clinical Acid Methyl Ester (5)4-Prop-2-ynyloxy-benzoic acid methyl ester and benzyl azide afforded 4-(1-benzyl-1,two,3-triazol-4-ylmethoxy)-benzoic acid methyl ester as white strong. Yields: 231.6mg (72%, below AgCl catalysis) Alisertib (MLN8237) and 174.3mg (54%, below silver complex catalysis). m.p. 145.7��C. IR (ATR) ��max /cm?1: 1753, 1650, 1600. 1H NMR (500MHz, CDCl3) ��/ppm: 3.87 (s, 3H), 5.22 (s, 2H), 5.53 (s, 2H), six.96�C6.99 (dd, 2H, J = 3Hz), 7.96�C7.99 (dd, 2H, J = 3Hz), 7.26�C7.28 (m, 2H), seven.35�C7.39 (m, 3H), 7.53 (s, 1H). 13C NMR (125MHz, CDCl3) ��/ppm: 51.8 (CH3), 54.3 (CH2), 62.one (CH2), 114.2 (two �� CH), 122.seven (C), 123.1 (CH), 127.6 (two �� CH), 128.8 (CH), 129.4 (two �� CH), 131.six (2 �� CH), 134.0 (C), 143.9 (C), 161.8 (C), 166.7 (C).



MS (EI+) m/z (%): 323 [M]+ (15), 91 [C6H5CH2]+ (a hundred), 144 [C10H10N]+ (95), 172 [C10H10N3]+ (45). HRMS (EI): calcd. for C18H17N3O3: 323.1270; uncovered: 323.1274.2.seven. 1-Benzyl-4-(4-methoxy-phenoxymethyl)-1,two,3-triazole (six)1-Methoxy-4-prop-2-ynyloxy-benzene and benzyl azide afforded 1-benzyl-4-(4-methoxy-phenoxymethyl)-1,2,3-triazole as white strong. Yields: 162.3mg (55%, beneath AgCl catalysis) and 189.3mg (64%, below silver complex catalysis). m.p. 92.7��C (lit. 92-93��C) [14]. IR (ATR) ��max /cm?1: 2950, 1650, and 1600. 1H NMR (500MHz, CDCl3) ��/ppm: three.76 (s, 3H), five.13 (s, 2H), five.52 (s, 2H), six.80�C6.82 (dd, 2H, J = 2Hz, J = 9Hz), six.88�C6.90 (dd, 2H, J = 2Hz, J = 9Hz), seven.26-7.27 (m, 2H), seven.36-7.38 (m, 3H), and 7.50 (s, 1H). 13C NMR (125MHz, CDCl3) ��/ppm: 54.2 (CH3), 55.six (CH2), 62.eight (CH2), 114.

6 (2 �� CH), 115.

9 (two �� CH), 122.9 (CH), 128.1 (two �� CH), 128.8 (CH), 129.one (two �� CH), 134.5 (C), 144.9 (C), 152.4 (C), and 154.3 (C). MS (EI+) m/z (percent): 295 [M]+ (forty), 91 [C6H5CH2]+ (one hundred), 144 [C10H10N]+ (80), 124 [C7H8O2]+ (68), and 172 [C10H10N3]+ (five).two.8. 1-Benzyl-4-(4��-chlorophenoxymethyl)-1,2,3-triazole (7)1-Chloro-4-prop-2-ynyloxy-benzene and benzyl azidehttp://www.selleckchem.com/autophagy.html afforded 1-benzyl-4-(4��-chlorophenoxymethyl)-1,2,3-triazole as white sound. Yields: 201.6mg (67%, below AgCl catalysis) and 216.4mg (72%, beneath silver complicated catalysis). 102.3��C (lit. 102-103��C) [15]. IR (ATR) ��max /cm?one: 1650, and 1600. 1H NMR (500MHz, CDCl3) ��/ppm: five.16 (s, 2H), five.54 (s, 2H), 6.89�C6.92 (dd, 2H, J = 2Hz, J = 9Hz), seven.22�C7.25 (dd, 2H, J = 3Hz, J = 9Hz), seven.27�C7.thirty (m, 2H), seven.38�C7.

40 (m, 3H), and seven.53 (s, 1H).

13C NMR (125MHz, CDCl3) ��/ppm: 54.two (CH2), 62.two (CH2), 116.0 (2 �� CH), 122.six (CH), 126.one (C), 128.0 (2 �� CH), 128.8, 129.four (2 �� CH) 129.7 (two �� CH), 134.3 (C), 144.one (C), and 156.7 (C).