# Design, Synthesis and Antifungal Activity of Novel Benzoylcarbamates Bearing a Pyridine Moiety
## 2 Materials and Methods
### Synthesis
#### 2.1.4 General Procedure for the Synthesis of Substituted Benzoylcarbamates **(4a-4j)**
98.9-99.4\({}^{\circ}\)C. \({}^{1}\)H NMR (CDCl\({}_{3}\)) \(\delta\) 1.07 (s, 9H, C(CH\({}_{3}\))\({}_{3}\)), 2.78-2.84 (m, 1H, CH\({}_{2}\)), 2.99 (dd, \(J\) = 2.8, 11.6 Hz, 1H, CH\({}_{2}\)), 3.85 (s, 3H, OCH\({}_{3}\)), 5.01 (q, \(J\) = 8.0 Hz, 1H, CH), 7.09-7.63 (m, 6H, Ar-H), 7.90 (bs, 1H, NH), 8.43-8.48 (m, 2H, Py-H). \({}^{13}\)C NMR (CDCl\({}_{3}\)) \(\delta\) 164.69, 151.07, 150.49, 147.95, 136.64, 134.92, 133.56, 129.74, 123.45, 123.25, 119.39, 119.16, 112.89, 83.29, 55.48, 35.06, 33.35, 25.97. IR (KBr)\(v_{\rm max}\) 3307(N-H), 1770 (C=O of carbamate), 1697 (C=O of benzoyl), 1394 and 1363 (C-H of \(t\)-butyl) cm\({}^{-1}\). Analysis calculated for C\({}_{20}\)H\({}_{24}\)N\({}_{2}\)O\({}_{4}\): C 67.40, H 6.79, N 7.86; found: C 67.65, H 6.86, N 7.54%. **3,3-Dimethyl-1-(pyridin-3-yl)butan-2-yl (2-chlorobenzoyl)carbamate (4f). ** Yield 87%, m.p. 119-120 \({}^{\circ}\)C. \({}^{1}\)H NMR (CDC\({}_{3}\)) \(\delta\) 1.03 (s, 9H, C(CH\({}_{3}\))\({}_{3}\)), 2.72-2.78 (m, 1H, CH\({}_{2}\)), 2.96 (dd, \(J\) = 2.4, 12.0 Hz, 1H, CH\({}_{2}\)), 4.95 (q, \(J\) = 8.4 Hz, 1H, CH), 7.19-7.59 (m, 6H, Ar-H), 8.29 (s, 1H, Py-H), 8.42 (s, 1H, Py-H) 8.75 (bs, 1H, NH). \({}^{13}\)C NMR (CDC\({}_{3}\)) \(\delta\) 166.32, 150.61, 150.19, 147.58, 136.73, 134.59, 133.41, 131.57, 130.54, 129.78, 129.20, 126.91, 123.54, 82.91, 35.01, 33.25, 25.90. IR (KBr)\(v_{\rm max}\) 3225(N-H), 1759 (C=O of carbamate), 1683 (C=O of benzoyl), 1395 and 1365 (C-H of \(t\)-butyl) cm\({}^{-1}\). Analysis calculated for C\({}_{19}\)H\({}_{21}\)ClN\({}_{2}\)O\({}_{3}\): C 63.24, H 5.87, N 7.76; found: C 62.94, H 5.71, N 7.98%. **3,3-Dimethyl-1-(pyridin-3-yl)butan-2-yl (3-chlorobenzoyl)carbamate (4g). ** Yield 84%, m.p. 117-118\({}^{\circ}\)C. \({}^{1}\)H NMR (CDC\({}_{3}\)) \(\delta\) 1.02 (s, 9H, C(CH\({}_{3}\))\({}_{3}\)), 2.71-2.77 (m, 1H, CH\({}_{2}\)), 2.96 (dd, \(J\) = 2.4, 11.6 Hz, 1H, CH\({}_{2}\)), 4.93 (q, \(J\) = 8.4 Hz, 1H, CH), 6.86-7.57 (m, 6H, Ar-H), 8.32 (s, 1H, Py-H), 8.41 (s, 1H, Py-H), 9.40 (bs, 1H, NH). \({}^{13}\)C NMR (CDC\({}_{3}\)) \(\delta\) 164.38, 151.39, 150.34, 147.76, 136.78, 134.99, 134.72, 133.63, 132.62, 129.87, 128.11, 125.99, 123.47, 83.41, 35.02, 33.34, 25.93. IR (KBr)\(v_{\rm max}\) 3265(N-H), 1748 (C=O of carbamate), 1683 (C=O of benzoyl), 1395 and 1366 (C-H of \(t\)-butyl) cm\({}^{-1}\). Analysis calculated for C\({}_{19}\)H\({}_{21}\)ClN\({}_{2}\)O\({}_{3}\): C 63.24, H 5.87, N 7.76; found: C 63.10, H 5.96, N 7.88%. **3,3-Dimethyl-1-(pyridin-3-yl)butan-2-yl (4-chlorobenzoyl)carbamate (4h). ** Yield 82%, m.p. 129-131\({}^{\circ}\)C. \({}^{1}\)H NMR (CDCl\({}_{3}\)) \(\delta\) 1.06 (s, 9H, C(CH\({}_{3}\))\({}_{3}\)), 2.77-2.83 (m, 1H, CH\({}_{2}\)), 2.98 (d, \(J\) = 14.4 Hz, 1H, CH\({}_{2}\)), 4.99 (q, \(J\) = 8.4 Hz, 1H, CH), 7.21-7.64 (m, 6H, Ar-H), 8.41-8.44 (m, 2H, Py-H), 8.77 (bs, 1H, NH). \({}^{13}\)C NMR (CDC\({}_{3}\)) \(\delta\) 164.82, 151.44, 150.36, 147.75, 139.11, 136.85, 133.70, 131.57, 129.38, 128.85, 123.52, 83.32, 35.02, 33.36, 25.94. IR (KBr)\(v_{\rm max}\) 3369 (N-H), 1776 (C=O of carbamate), 1689 (C=O of benzoyl), 1390 and 1367 (C-H of \(t\)-butyl) cm\({}^{-1}\). Analysis calculated for C\({}_{19}\)H\({}_{21}\)ClN\({}_{2}\)O\({}_{3}\): C 63.24, H 5.87, N 7.76; found: C 63.65, H 5.83, N 7.98%. **3,3-Dimethyl-1-(pyridin-3-yl)butan-2-yl (2-bromobenzoyl)carbamate (4i). ** Yield 84%; m.p. 114-115\({}^{\circ}\)C. \({}^{1}\)H NMR (CDC\({}_{3}\)) \(\delta\) 1.03 (s, 9H, C(CH\({}_{3}\))\({}_{3}\)), 2.72-2.79 (m, 1H, CH\({}_{2}\)), 2.97 (d, \(J\) = 13.6 Hz, 1H, CH\({}_{2}\)), 4.98 (q, \(J\) = 8.4 Hz, 1H, CH), 7.17-7.60 (m, 6H, Ar-H), 8.42 (s, 1H, Py-H), 9.35 (bs, 1H, NH). \({}^{13}\)C NMR (CDC\({}_{3}\)) \(\delta\) 150.45, 150.37, 147.89, 136.77, 136.62, 133.35, 132.97, 131.64, 128.96, 127.43, 123.31, 118.86, 83.23, 35.03, 33.29, 25.93. IR (KBr)\(v_{\rm max}\) 3260 (N-H), 1769 (C=O of carbamate), 1702 (C=O of benzoyl), 1394 and 1363 (C-H of \(t\)-butyl) cm\({}^{-1}\). Analysis calculated for C\({}_{19}\)H\({}_{21}\)BrN\({}_{2}\)O\({}_{3}\): C 56.31, H 5.22, N 6.91; found: C 56.68, H 5.20, N 7.14%.