.three, 129.3, 128.eight, 128.four, 128.2, 127.eight, 127.7, 126.two, 121.7, 43.9, 43.8. IR (neat): 3229, 2361, 1628, 1554, 1328 cm-1. HRMS (ESI) m/z calcd. For C18H17N2O (M+H)+ 277.1341, identified 277.1339. N-Benzyl-2-(p-tolyl)acetamide (6b).31–General process B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:four) supplied the title compound as a white strong in 75 yield (90 mg). Spectral data have been in accordance with those published. mp 13435 (lit. 136). 1H NMR (500 MHz, CDCl3): 7.33 (t, J = 7.two Hz, 2H), 7.27-7.26 (m, 1H), 7.21 (d, J = 7.two Hz, 2H), 7.18 (s, 4H), 5.67 (br s, 1H), four.41 (d, J = five.6 Hz, 2H), three.60 (s, 2H), two.33 (s, 3H). 13C NMR (125.eight MHz, CDCl3): 171.3, 138.four, 137.SN-001 In stock two, 131.8, 129.9, 129.five, 128.eight, 127.six, 127.five, 43.7, 43.six, 21.two. N-Cyclopropyl-2-(p-tolyl)acetamide (6c)–General procedure B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:4) offered the title compound as a white solid in 67 yield (63 mg). mp 11718 . 1H NMR (500 MHz, CDCl3): 7.BCA Autophagy 16-7.14 (m, 4H), 5.43 (br s, 1H), 3.50 (s, 2H), 2.67-2.63 (m, 1H), two.34 (s, 3H), 0.71 (dd, J =7.0, 1.3 Hz, 2H), 0.39-0.38 (m, 2H). 13C NMR (125.eight MHz, CDCl3): 172.9, 137.0, 132.0, 129.7, 129.three, 43.3, 22.9, 21.two, six.6. IR (neat): 3280, 1644, 1545, 1266 cm-1. HRMS (ESI) m/z calcd. For C12H16NO (M+H)+ 190.1232, discovered 190.1238. N-Cyclopropyl-2-(furan-3-yl)acetamide (6d)–General procedure B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:4) provided the title compound as a white solid in 70 yield (58 mg).PMID:24518703 mp 602 . 1H NMR (500 MHz, CDCl3): 7.43 (d, J = 1.3 Hz, 1H), 7.37 (s, 1H), six.33 (s, 1H), 5.77 (br s, 1H), three.37 (s, 2H), two.71-2.68 (m, 1H), 0.77 (q, J = 6.9 Hz, 2H), 0.45 (dd, J = two.2, 1.1 Hz, 2H). 13C NMR (125.8 MHz, CDCl3): 172.1, 143.7, 140.8, 118.4, 111.three, 32.9, 22.eight, 6.6. IR (neat): 3287, 1650, 1539, 1022 cm-1. HRMS (ESI) m/z calcd. For C9H12NO2 (M+H)+ 166.0868, identified 166.0870. N-Cyclopropyl-2-(naphthalen-1-yl)acetamide (6e).32–General process B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:four) supplied the title compound as a white solid in 71 yield (80 mg). Spectral data had been in accordance with these published. mp 13436 (lit. 140-141). 1H NMR (500 MHz, CDCl3): 7.96 (t, J = 6.1 Hz, 1H), 7.91 (q, J = 6.7 Hz, 1H), 7.85 (d, J = 8.two Hz, 1H), 7.55-7.52 (m, 2H), 7.46-7.43 (m, 1H), 7.38-7.36 (m, 1H), five.38 (br s, 1H), three.99 (s, 2H), two.60-2.57 (m, 1H), 0.65 (q, J = six.3 Hz, 2H), 0.26-0.25 (m, 2H). 13C NMR (125.eight MHz, CDCl3): 172.two, 133.9, 131.9, 131.1, 128.7, 128.4, 128.1, 126.7, 126.1, 125.5, 123.7, 41.7, 22.6, six.four. N-Cyclopropyl-2-(isoquinolin-5-yl)acetamide (6f)–General process B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:4) supplied the title compound as a light orange solid in 62 yield (70 mg). mp 14547 . 1H NMR (500 MHz, CDCl3): 9.26 (s, 1H), 8.57-8.56 (m, 1H), 7.94-7.92 (m, 1H), 7.78 (t, J =4.5 Hz, 1H), 7.58-7.57 (m, 2H), five.49 (br s, 1H), 3.94 (s, 2H), 2.63-2.61 (m, 1H), 0.68 (dd, J = 7.0, 1.4 Hz,NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptJ Org Chem. Author manuscript; obtainable in PMC 2014 April 19.Molander et al.Page2H), 0.31 (td, J = 2.five, 1.1 Hz, 2H). 13C NMR (125.8 MHz, CDCl3): 171.7, 153.two, 143.7, 135.0, 132.two, 130.9, 129.1, 127.8, 127.two, 117.0, 40.7, 23.0, 6.6. IR (neat): 3281, 1648, 1544 cm-1. HRMS (ESI) m/z calcd. For C14H15N2O (M+H)+ 227.1184, located 227.1190.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptSupplementary MaterialRefer to Web version.
