Thompson et al.
(solid)/cm-1 3131, 2969, 1706, 1495, 1311, 1254, 1172, 1140, 1031,
843, 767; m/z (ESI) 405 ([M + H]+); HRMS found 405.1435
(C21H20F3N2O3 requires 405.1426).
1486, 1280, 1092, 1079, 1012, 849, 754, 724, 689, 673; m/z (ESI)
391 ([M + H]+); HRMS found 391.0977 (C21H16ClN4O2 requires
391.0962).
N-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-4-phenyloxazol-5-yl)-3-
methylbutanamide (1j): δH (400 MHz, DMSO-d6) 10.41 (s, 1H),
7.79 (d, 2H, J ) 7.0), 7.45 (t, 2H, J ) 7.5), 7.36 (t, 1H, J ) 7.5),
6.64 (s, 1H), 4.17 (s, 3H), 2.30 (d, 2H, J ) 7.0), 2.20 (s, 3H), 2.09
(septet, 1H, J ) 7.0), 0.96 (d, 6H, J ) 7.0); δC (100 MHz, DMSO-
d6) 172.6, 150.2, 146.7, 138.1, 130.8, 130.1, 129.9, 128.6, 128.1,
125.8, 106.6, 44.3, 25.4, 22.2, 12.9; νmax (solid)/cm-1 3238, 2954,
1670, 1635, 1508, 1480, 1370, 1279, 1216, 1076, 1010, 766, 725,
687; m/z (ESI) 339 ([M + H]+); HRMS found 339.1833
(C19H23N4O2 requires 339.1821).
N-(2-(Benzo[b]thiophene-2-yl)-4-benzyloxazol-5-yl)furan-2-
carboxamide (1k): δH (400 MHz, CDCl3) 7.89-7.80 (m, 3H), 7.70
(br s, 1H), 7.53-7.49 (m, 1H), 7.44-7.37 (m, 2H), 7.34 (d, 2H, J
) 7.5), 7.31-7.24 (m, 3H), 7.19 (t, 1H, J ) 7.5), 6.58 (dd, 1H, J
) 1.5, 3.5), 4.00 (s, 2H); δC (100 MHz, CDCl3) 156.5, 154.7, 146.5,
145.0, 140.4, 139.5, 137.7, 137.2, 133.6, 129.5, 128.9, 128.5, 126.5,
125.9, 124.9, 124.6, 124.4, 122.5, 116.7, 112.7, 32.4; νmax (solid)/
cm-1 3360, 1697, 1656, 1583, 1488, 1454, 1272, 1163, 1014, 746,
706, 695; m/z (ESI) 401 ([M + H]+); HRMS found 401.0953
(C23H17N2O3S requires 401.0960). The identity of 1k was also
confirmed by X-ray crystallography, following crystallization from
CH2Cl2-hexane.
N-(2-(Benzo[b]thiophene-2-yl)-4-benzyloxazol-5-yl)-4-meth-
oxybenzamide (1l). δH (400 MHz, DMSO-d6) 10.58 (s, 1H),
8.09-7.93 (m, 5H), 7.50-7.42 (m, 2H), 7.37-7.26 (m, 4H),
7.24-7.17 (m, 1H), 7.14-7.08 (m, 2H), 3.91-3.81 (m, 5H); δC
(100 MHz, DMSO-d6) 166.0, 162.6, 153.3, 140.1, 139.4, 139.3,
138.4, 132.6, 130.0, 128.8, 128.3, 126.2, 125.2, 124.8, 124.6, 124.3,
122.7, 113.9, 55.5, 31.1; νmax (solid)/cm-1 3214, 1660, 1638, 1604,
1477, 1254, 1172, 1022, 840, 745, 699; m/z (ESI) 441 ([M + H]+);
HRMS found 441.1276 (C26H21N2O3S requires 441.1273).
N-(2-(Benzo[b]thiophene-2-yl)-4-benzyloxazol-5-yl)-4-chlo-
robenzamide (1m): δH (400 MHz, DMSO-d6) 10.83 (s, 1H),
8.07-7.93 (m, 5H), 7.66 (d, 2H, J ) 8.5), 7.49-7.42 (m, 2H),
7.34-7.26 (m, 4H), 7.23-7.17 (m, 1H), 3.87 (s, 2H); δC (100 MHz,
DMSO-d6) 165.7, 153.4, 139.6, 139.4, 139.3, 138.2, 137.4, 132.6,
131.3, 129.9, 128.76, 128.72, 128.3, 126.2, 125.2, 124.9, 124.4,
122.7, 31.1; νmax (solid)/cm-1 3221, 1664, 1641, 1477, 1296, 1277,
1258, 1093, 1015, 841, 746, 705, 695, 680, 649; m/z (ESI) 445
([M + H]+); HRMS found 445.0791 (C25H18ClN2O2S requires
445.0778).
N-(2-(Benzo[b]thiophene-2-yl)-4-benzyloxazol-5-yl)-3-methyl-
butanamide (1n): δH (400 MHz, DMSO-d6) 10.24 (s, 1H),
8.07-7.92 (m, 3H), 7.50-7.41 (m, 2H), 7.35-7.26 (m, 4H),
7.25-7.18 (m, 1H), 3.78 (s, 2H), 2.25 (d, 2H, J ) 7.0), 2.15-2.04
(m, 1H), 0.97 (d, 6H, J ) 6.5); δC (100 MHz, DMSO-d6) 172.8,
153.5, 140.3, 139.8, 139.7, 138.9, 132.2, 129.3, 129.2, 128.8, 126.7,
126.6, 125.7, 125.3, 124.6, 123.2, 44.7, 31.5, 25.9, 22.7; νmax (solid)/
cm-1 3231, 2960, 1668, 1646, 1511, 1261, 838, 746, 692, 649,
600; m/z (ESI) 391 ([M + H]+); HRMS found 391.1484
(C23H23N2O2S requires 391.1480).
N-(4-Isopropyl-2-(4-methoxyphenyl)oxazol-5-yl)-4-methoxy-
benzamide (1c): δH (400 MHz, CDCl3) 8.29 (br s, 1H), 7.90-7.81
(m, 4H), 6.90 (d, 2H, J ) 8.5), 6.84 (d, 2H, J ) 8.5), 3.83 (s, 3H),
3.77 (s, 3H), 2.87 (septet, 1H, J ) 7.0), 1.25 (d, 6H, J ) 7.0); δC
(100 MHz, CDCl3) 162.9, 161.1, 158.4, 139.8, 135.4, 129.6, 127.8,
124.9, 120.5, 114.0, 113.9, 55.37, 55.35, 25.8, 21.3; νmax (solid)/
cm-1 3258, 2968, 1666, 1650, 1605, 1500, 1283, 1253, 1180, 1024,
848, 836, 766, 746; m/z (ESI) 367 ([M + H]+); HRMS found
367.1657 (C21H23N2O4 requires 367.1658).
N-(4-Isopropyl-2-(thiophene-2-yl)oxazol-5-yl)furan-2-carbox-
amide (1d): δH (400 MHz, CDCl3) 7.86 (s, 1H), 7.65-7.62 (m,
1H), 7.58-7.56 (m, 1H), 7.43-7.40 (m, 1H), 7.31 (br s, 1H),
7.12-7.08 (m, 1H), 6.62-6.59 (m, 1H), 2.93 (septet, 1H, J ) 7.0),
1.31 (d, 6H, J ) 7.0); δC (100 MHz, CDCl3) 157.1, 154.8, 146.7,
145.0, 140.5, 133.8, 130.3, 128.0, 127.8, 127.6, 116.8, 112.8, 25.8,
21.2; νmax (solid)/cm-1 3219, 2971, 1673, 1645, 1585, 1507, 1290,
1055, 1016, 760, 737, 726; m/z (ESI) 303 ([M + H]+); HRMS
found 303.0798 (C15H15N2O3S requires 303.0803).
N-(4-Isopropyl-2-(thiophene-2-yl)oxazol-5-yl)-2-(trifluorome-
thyl)benzamide (1e): δH (400 MHz, DMSO-d6, 50 °C) 10.59 (s,
1H), 7.86 (d, 1H, J ) 8.0), 7.82 (t, 1H, J ) 7.5), 7.77-7.71 (m,
3H), 7.63 (d, 1H, J ) 3.5), 7.19 (t, 1H, J ) 4.5), 2.89 (septet, 1H,
J ) 7.0), 1.22 (d, 6H, J ) 7.0); δC (125 MHz, DMSO-d6, 50 °C)
167.0, 153.2, 138.2, 135.5, 134.5, 132.4, 130.4, 129.2, 129.0, 128.3,
128.1, 127.3, 126.33-126.24 (m), 126.0 (q, J ) 31.5), 123.4 (q, J
) 272), 24.6, 20.9; νmax (solid)/cm-1 3148, 2966, 1708, 1652, 1515,
1488, 1313, 1267, 1166, 1125, 1106, 1052, 1034, 765, 717; m/z
(ESI) 381 ([M + H]+); HRMS found 381.0902 (C18H16F3N2O2S
requires 381.0885).
N-(4-Isopropyl-2-(thiophene-2-yl)oxazol-5-yl)-4-methoxybenz-
amide (1f): δH (400 MHz, CDCl3) 8.17 (s, 1H), 7.85 (d, 2H, J )
8.0), 7.56 (d, 1H, J ) 3.0), 7.39-7.36 (m, 1H), 7.06 (dd, 1H, J )
4.0, 5.0), 6.88 (d, 2H, J ) 9.0), 3.81 (s, 3H), 2.89 (septet, 1H, J )
7.0), 1.25 (d, 6H, J ) 7.0); δC (100 MHz, CDCl3) 166.7, 163.0,
154.6, 140.1, 135.4, 130.3, 129.7, 127.9, 127.8, 127.5, 124.8, 113.9,
55.4, 25.8, 21.3; νmax (solid)/cm-1 3232, 2966, 1667, 1641, 1604,
1579, 1485, 1253, 1175, 1022, 843, 765, 704; m/z (ESI) 343 ([M
+ H]+); HRMS, found 343.1118 (C18H19N2O3S requires 343.1116).
N-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-4-phenyloxazol-5-yl)fu-
ran-2-carboxamide (1g): δH (400 MHz, CDCl3) 7.84-7.79 (m,
2H), 7.57 (br s, 1H), 7.40 (t, 2H, J ) 7.5), 7.33 (t, 2H, J ) 7.5),
6.60 (dd, 1H, J ) 1.5, 3.5), 6.56 (s, 1H), 4.25 (s, 3H), 2.29 (s,
3H); δC (100 MHz, CDCl3) 157.2, 151.3, 147.6, 146.5, 145.4, 135.3,
133.1, 130.7, 130.2, 128.7, 128.3, 126.4, 117.1, 112.8, 107.0, 39.0,
13.3; νmax (solid)/cm-1 3123, 2946, 1674, 1585, 1506, 1448, 1279,
1075, 1007, 759, 730, 693, 679; m/z (ESI) 349 ([M + H]+); HRMS
found 349.1302 (C19H17N4O3 requires 349.1301).
N-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-4-phenyloxazol-5-yl)-4-
methoxybenzamide (1h): δH (400 MHz, CDCl3) 8.28 (s, 1H), 7.89
(d, 2H, J ) 8.5), 7.82-7.77 (m, 2H), 7.37 (t, 2H, J ) 8.0), 7.30
(tt, J ) 2.0, 7.5), 6.93 (d, 2H, J ) 8.5), 6.51 (s, 1H), 4.23 (s, 3H),
3.87 (s, 3H), 2.27 (s, 3H); δC (100 MHz, CDCl3) 166.4, 163.3,
151.2, 147.6, 136.6, 132.8, 130.8, 130.4, 129.8, 128.7, 128.2, 126.3,
124.5, 114.1, 107.0, 55.5, 39.0, 13.3; νmax (solid)/cm-1 3276, 1661,
1636, 1602, 1454, 1439, 1255, 1200, 1175, 1025, 1005, 994, 846,
765, 730, 694; m/z (ESI) 389 ([M + H]+); HRMS found 389.1627
(C22H21N4O3 requires 389.1614).
N-(2-(4-Chlorobenzyl)-4-(thiophene-2-yl)oxazol-5-yl)furan-2-
carboxamide (1o): δH (400 MHz, CDCl3) 7.91 (s, 1H), 7.57 (s,
1H), 7.38-7.27 (m, 7H), 7.06 (dd, 1H, J ) 3.5, 5.0), 6.64-6.60
(m, 1H), 4.12 (s, 2H); δC (100 MHz, CDCl3) 160.4, 157.5, 146.9,
145.7, 134.9, 133.8, 133.6, 132.9, 130.7, 129.3, 128.1, 126.1, 125.5,
117.5, 113.3, 34.8; νmax (solid)/cm-1 3244, 1665, 1509, 1491, 1464,
1298, 1185, 1022, 763, 704; m/z (ESI) 385 ([M + H]+); HRMS
found 385.0399 (C19H14ClN2O3S requires 385.0414).
4-Chloro-N-(2-(1,3-dimethyl-1H-pyrazol-5-yl)-4-phenyloxazol-
5-yl)benzamide (1i): δH (400 MHz, DMSO-d6) 11.14 (s, 1H), 8.09
(d, 2H, J ) 8.0), 7.87-7.81 (m, 2H), 7.69 (d, 2H, J ) 7.5), 7.47
(t, 2H, J ) 7.0), 7.37 (t, 1H, J ) 7.5), 6.71 (s, 1H), 4.22 (s, 3H),
2.22 (s, 3H); δC (100 MHz, DMSO-d6) 165.8, 150.6, 146.8, 137.9,
137.7, 131.5, 131.0, 130.0, 129.9, 129.8, 128.9, 128.8, 128.2, 125.8,
106.7, 38.7, 13.0; νmax (solid)/cm-1 3226, 1663, 1623, 1592, 1508,
N-(2-(4-Chlorobenzyl)-4-(thiophene-2-yl)oxazol-5-yl)-4-meth-
oxybenzamide (1p): δH (400 MHz, DMSO-d6) 10.56 (s, 1H), 8.00
(d, 2H, J ) 8.5), 7.53 (d, 1H, J ) 5.5), 7.44 (d, 2H, J ) 8.5), 7.39
(d, 2H, J ) 8.5), 7.28-7.25 (m, 1H), 7.13-7.07 (m, 3H), 4.21 (s,
2H), 3.86 (s, 3H); δC (100 MHz, DMSO-d6) 166.8, 163.5, 160.6,
138.2, 135.3, 133.6, 132.6, 131.6, 130.8, 129.5, 128.6, 128.3, 126.9,
125.4, 125.2, 114.9, 56.4, 34.0; νmax (solid)/cm-1 3214, 1663, 1606,
3864 J. Org. Chem. Vol. 74, No. 10, 2009