Combinatorial Synthesis
4280±4295
Compound 105: Rf 0.18 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
6.2 Hz, 1H), 2.84 (t, J 5.8 Hz, 1H), 2.36 (s, 3H); 13C NMR (100 MHz,
CDCl3): d 164.2, 153.1, 148.1, 141.0, 129.7, 129.5, 129.2, 116.0, 114.3, 37.7,
37.4, 28.1, 11.9; HRMS (MALDI-FTMS): calcd for C16H17ClN2O4S2
3410, 1671, 1524, 1433, 1290, 1225, 1020, 831, 707 cm 1; 1H NMR (400 MHz,
CD3OD): d 7.21 (d, J 8.5 Hz, 2H), 7.11 (d, J 2.0 Hz, 1H), 6.94 (dd, J
8.2, 2.0 Hz, 1H), 6.68 (d, J 8.2 Hz, 1H), 6.54 (d, J 8.5 Hz, 2H), 3.69 (s,
2H), 3.46 (t, J 6.8 Hz, 2H), 2.71 (d, J 7.3 Hz, 2H); 13C NMR (125 MHz,
CD3OD): d 163.5, 152.1, 151.6, 150.4, 134.7, 130.2, 128.8, 116.7, 114.6,
109.0, 108.1, 38.4, 36.5, 28.1; HRMS (MALDI-FTMS): calcd for
[MH] : 401.0391, found: 401.0376.
Compound 117: Rf 0.18 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
3383, 1664, 1513, 1429, 1290, 1222, 1020, 951, 706 cm 1; 1H NMR (400 MHz,
CD3OD): d 7.11 (d, J 2.0 Hz, 1H), 6.95 (dd, J 7.0, 2.1 Hz, 1H), 6.69 (d,
J 8.2 Hz, 1H), 3.71 (s, 2H), 3.46 (t, J 6.8 Hz, 2H), 2.83 ± 2.71 (m, 6H);
13C NMR (100 MHz, CD3OD): d 166.1, 153.3, 153.2, 131.5, 130.4, 129.9,
121.4, 119.8, 117.5, 39.6, 38.8, 34.4, 28.9, 18.2; HRMS (MALDI-FTMS):
C17H18ClN3O3S2 [M] : 411.0473, found: 411.0469.
Compound 106: Rf 0.15 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
3381, 1654, 1591, 1503, 1431, 1360, 1196, 670 cm
;
1H NMR (500 MHz,
CDCl3): d 7.43 (d, J 8.5 Hz, 2H), 7.29 (d, J 2.0 Hz, 1H), 7.13 (dd, J
8.2, 2.0 Hz, 1H), 6.88 (d, J 8.2 Hz, 1H), 6.79 (m, 1H), 6.68 (d, J 8.8 Hz,
2H), 3.82 (s, 2H), 3.64 (d, J 6.2 Hz, 2H), 2.97 (s, 6H), 2.85 (t, J 6.2 Hz,
2H); 13C NMR (125 MHz, CDCl3): d 133.7, 129.6, 129.5, 129.3, 116.0,
113.5, 40.58, 37.47, 37.35, 28.0; HRMS (MALDI-FTMS): calcd for
calcd for C14H16ClN3O3S2 [MH] : 396.0214, found: 396.0205.
Compound 118: Rf 0.30 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
3415, 2916, 1661, 1513, 1433, 1319, 1226, 1152, 1023, 951, 706 cm 1; 1H NMR
(400 MHz, CD3OD): d 7.65 (dd, J 4.4, 0.6 Hz, 1H), 7.51 (dd, J 3.5,
1.2 Hz, 1H), 7.11 (d, J 2.3 Hz, 1H), 7.03 (dd, J 4.4, 3.8 Hz, 1H), 6.95 (dd,
J 8.2, 2.0 Hz, 1H), 6.68 (d, J 8.5 Hz, 1H), 3.71 (s, 2H), 3.42 (t, J
6.7 Hz, 2H), 3.15 (t, J 6.4 Hz, 2H), 2.67 (m, 4H); 13C NMR (100 MHz,
CD3OD): d 166.0, 154.8, 153.1, 146.1, 133.3, 133.2, 131.6, 129.9, 128.7,
120.3, 117.5, 105.5, 43.4, 39.7, 38.9, 30.1; HRMS (MALDI-FTMS): calcd for
C19H22ClN3O3S2 [MH] : 440.0864, found: 440.0854.
Compound 107: Rf 0.16 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
3381, 1656, 1531, 1426, 1209, 1015, 907, 804, 730 cm 1; 1H NMR (400 MHz,
CDCl3): d 8.30 (s, 1H), 7.41 (d, J 8.2 Hz, 2H), 7.30 (d, J 1.7 Hz, 1H),
7.13 ± 7.10 (m, 4H), 7.03 (m, 1H), 6.88 (d, J 8.5 Hz, 1H), 5.57 (s, 1H), 3.86
(s, 2H), 3.61 (q, J 6.2 Hz, 2H), 2.82 (t, J 6.2 Hz, 2H), 2.32 (s, 3H);
13C NMR (100 MHz, CDCl3): d 162.9, 152.9, 149.9, 137.6, 133.2, 129.9,
129.7, 129.5, 129.2, 128.9, 116.1, 37.7, 37.4, 28.1, 21.0; HRMS (MALDI-
C17H20ClN3O5S4 [MNa] : 531.9866, found: 531.9871.
Compound 119: Rf 0.22 (silica gel, EtOAc/hexanes 1:1); 1H NMR
(400 MHz, CD3OD): d 7.11 (d, J 2.0 Hz, 1H), 6.94 (dd, J 7.0, 2.3 Hz,
1H), 6.68 (d, J 8.2 Hz, 1H), 4.10 (q, J 7.0 Hz, 2H), 3.70 (m, 3H), 3.46
(td, J 7.1, 2.1 Hz, 2H), 3.00 (dd, J 7.2, 5.3 Hz, 1H), 2.86 (dd, J 7.0,
7.0 Hz, 1H), 2.76 (t, J 6.7 Hz, 2H); HRMS (MALDI-FTMS): calcd for
FTMS): calcd for C18H19ClN2O3S2 [MH] : 411.0598, found: 411.0592.
Compound 109: Rf 0.17 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
;
1H NMR (400 MHz,
3381, 1654, 1532, 1429, 1208, 1017, 737, 685 cm
C16H22ClN3O5S2 [MH] : 436.0762, found: 436.0774.
CDCl3): d 8.34 (s, 1H), 7.51 (dm, J 8.5 Hz, 2H), 7.32 ± 7.28 (m, 3H), 7.24
(tm, J 9.2 Hz, 1H), 7.14 (dm, J 7.3 Hz, 1H), 7.20 (m, 1H), 6.87 (dd, J
8.2, 0.88 Hz, 1H), 3.86 (s, 2H), 3.61 (q, J 6.2 Hz, 2H), 2.84 (t, J 5.6 Hz,
2H); 13C NMR (100 MHz, CDCl3): d 162.9, 152.9, 149.9, 136.7, 129.7,
129.5, 129.2, 129.1, 127.9, 127.2, 119.6, 116.1, 37.7, 37.5, 28.1; HRMS
Compound 121: 1H NMR (400 MHz, CD3OD): d 7.64 (d, J 8.2 Hz, 1H),
7.26 (d, J 7.9 Hz, 1H), 7.11 (d, J 1.7 Hz, 1H), 6.94 (dd, J 8.5, 2.1 Hz,
1H), 6.68 (d, J 8.5 Hz, 1H), 3.70 (s, 3H), 3.39 (t, J 7.0 Hz, 1H), 3.30 (t,
J 7.0 Hz, 2H), 3.05 (t, J 7.0 Hz, 1H), 2.66 ± 2.58 (m, 2H), 2.50 (t, J
7.0 Hz, 2H).
(MALDI-FTMS): calcd for C17H17ClN2O3S2 [MH] : 397.0442, found:
Compound 122: Rf 0.23 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
397.0436.
1
3384, 2919, 1660, 1502, 1431, 1321, 1152, 1020 cm
;
1H NMR (400 MHz,
Compound 110: Rf 0.13 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
CD3OD): d 7.69 (d, J 7.0 Hz, 2H), 7.11 (d, J 2.0 Hz, 1H), 6.96 ± 6.93
(m, 3H), 6.68 (d, J 8.2 Hz, 1H), 3.75 (s, 3H), 3.70 (s, 2H), 3.40 (t, J
6.5 Hz, 2H), 3.04 (t, J 6.5 Hz, 2H), 2.66 ± 2.59 (m, 4H); 13C NMR
(100 MHz, CD3OD): d 166.0, 164.6, 153.2, 152.8, 133.4, 131.5, 130.4, 130.3,
129.8, 121.4, 117.5, 115.5, 56.3, 43.1, 39.8, 39.0, 38.4, 28.9; MS (EIS): calcd for
1
3384, 1657, 1512, 1338, 1208, 907, 847, 733 cm
;
1H NMR (400 MHz,
CDCl3): d 8.15 (d, J 4.7 Hz, 2H), 7.62 (d, J 6.8 Hz, 2H), 7.29 (d, J
2.1 Hz, 1H), 7.14 (dd, J 8.2, 2.1 Hz, 2H), 6.96 (m, 1H), 6.87 (d, J 8.2 Hz,
1H), 5.57 (brs, 1H), 3.85 (s, 2H), 3.59 (q, J 6.2 Hz, 2H), 2.90 (t, J
6.4 Hz, 2H); 13C NMR (100 MHz, CDCl3): d 163.5, 152.9, 150.0, 129.7,
129.5, 129.1, 128.0, 126.1, 124.1, 119.6, 116.1, 38.0, 37.7, 28.0, 14.2; MS (ESI):
C20H24ClN3O6S3 [MNa] : 556, found: 556.
calcd for C17H16ClN3O5S2 [MH] : 442, found: 442.
Compound 123: Rf 0.26 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
3283, 1660, 1514, 1336, 1015, 848, 739, 692 cm
;
1H NMR (400 MHz,
Compound 112: Rf 0.45 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
;
1H NMR (400 MHz,
CDCl3): d 8.15 (d, J 9.1 Hz, 2H), 7.61 (d, J 9.1 Hz, 4H), 7.42 ± 7.32 (m,
8H), 5.25 (s, 2H), 3.71 (q, J 6.2 Hz, 2H), 2.92 (t, J 6.4 Hz, 2H);
13C NMR (100 MHz, [D6]DMSO): d 163.6, 161.0, 159.0, 152.1, 151.5,
132.2, 131.4, 130.2, 128.7, 125.6, 119.4, 116.7, 116.4, 116.2, 40.4, 38.8, 37.3,
3349, 1595, 1489, 1429, 1294, 1218, 1021, 825 cm
CD3OD): d 9.12 (s, 1H), 8.32 (dd, J 8.8, 2.6 Hz, 1H), 7.81 (d, J 9.1 Hz,
1H), 7.09 (d, J 2.0 Hz, 1H), 6.93 (dd, J 8.5, 2.0 Hz, 1H), 6.65 (d, J
8.2 Hz, 1H), 3.69 (s, 2H), 3.45 (t, J 6.4 Hz, 2H), 2.92 (t, J 6.2 Hz, 2H);
13C NMR (100 MHz, CD3OD): d 169.2, 164.1, 153.3, 152.8, 146.2, 144.0,
133.3, 131.5, 130.3, 129.8, 121.1, 117.5, 39.5, 39.2, 28.9; HRMS (MALDI-
28.1; HRMS (MALDI-FTMS): calcd for C23H21N3O4S2 [MNa] : 490.0866,
found: 490.0866.
FTMS): calcd for C16H15ClN4O5S2 [MH] : 443.0245, found: 443.0246.
Compound 124: Rf 0.23 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
3400, 1657, 1534, 1465, 1441, 1254, 1013, 811, 693 cm 1; 1H NMR (500 MHz,
CDCl3): d 7.61 ± 7.59 (m, 2H), 7.41 ± 7.33 (m, 12H), 5.23 (s, 2H), 3.70 (q,
J 7.7 Hz, 2H), 2.86 (t, J 7.7 Hz, 2H); 13C NMR (100 MHz, CDCl3): d
163.1, 152.8, 132.2, 131.1, 130.2, 129.4, 128.6, 128.5, 128.4, 128.1, 126.8, 37.6,
Compound 113: Rf 0.10 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
3356, 1656, 1495, 1040, 729 cm 1; 1H NMR (400 MHz, CDCl3): d 8.89 (d,
J 4.4 Hz, 1H), 8.17 (d, J 8.2 Hz, 1H), 8.10 (d, J 7.3 Hz, 1H), 7.64 (d,
J 8.2 Hz, 1H), 7.54 (dd, J 7.6 Hz, 1H), 7.46 (dd, J 8.5, 4.4 Hz, 1H), 7.29
(d, J 1.7 Hz, 1H), 7.16 (m, 1H), 7.12 (dd, J 8.5, 1.7 Hz, 1H), 6.86 (q, J
8.2 Hz, 1H), 3.83 (s, 2H), 3.61 (q, J 6.2 Hz, 2H); 13C NMR (100 MHz,
CDCl3): d 164.1, 153.2, 150.0, 149.5, 136.7, 136.2, 129.7, 129.3, 129.4, 128.7,
128.5, 126.8, 125.6, 125.3, 121.8, 119.7, 116.1, 38.1, 36.7, 28.1; HRMS
37.5; HRMS (MALDI-FTMS): calcd for C23H21BrN2O2S2 [MH] :
501.0301, found: 501.0287.
Compound 125: Rf 0.63 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
2932, 1665, 1541, 1409, 1276, 1005, 911, 736, 693 cm 1; 1H NMR (400 MHz,
CDCl3): d 8.42 (m, 1H), 7.90 (s, 2H), 7.63 (dd, J 7.6, 1.2 Hz, 2H), 7.39 ±
7.32 (m, 6H), 7.29 ± 7.22 (m, 2H), 5.23 (s, 2H), 3.76 (q, J 5.5 Hz, 2H), 3.66
(t, J 6.4 Hz, 2H), 3.09 (dd, J 5.8, 4.1 Hz, 2H), 1.74 (q, J 6.7 Hz, 2H),
1.01 (t, J 7.3 Hz, 3H); 13C NMR (100 MHz, CDCl3): d 163.1, 153.7,
151.2, 144.6, 137.4, 131.1, 130.1, 129.6, 128.6, 128.3, 128.2, 128.1, 127.8, 126.5,
76.8, 70.4, 40.6, 36.9, 22.3, 10.3.
(MALDI-FTMS): calcd for C16H18ClN3O3S2 [MH] : 448.0551, found:
448.0542.
Compound 114: Rf 0.50 (silica gel, EtOAc/hexanes 1:1); 1H NMR
(400 MHz, CDCl3): d 9.03 (m, 1H), 8.28 (dd, J 6.4, 1.2 Hz, 1H), 8.21
(dd, J 5.8, 0.8 Hz, 1H), 8.02 (brs, 1H), 7.75 (d, J 5.8 Hz, 1H), 7.65 (d,
J 6.2 Hz, 1H), 7.57 ± 7.54 (m, 1H), 7.51 (s, 2H), 3.89 (s, 2H), 3.74 (q, J
5.0 Hz, 2H), 3.00 (t, J 4.9 Hz, 2H); 13C NMR (100 MHz, CDCl3): d
163.2, 151.3, 149.6, 149.0, 141.6, 136.6, 136.5, 132.3, 131.1, 128.1, 128.0, 127.0,
126.9, 125.8, 125.3, 123.9, 123.5, 122.3, 111.7, 38.1, 36.4, 27.5.
Compound 127: Rf 0.76 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
3281, 2920, 1708, 1647, 1596, 1438, 1325, 1225, 1156, 1022, 952, 744 cm
;
1H NMR (400 MHz, CD3OD): d 7.56 (d, J 8.2 Hz, 2H), 7.38 (d, J
7.0 Hz, 2H), 7.24 ± 7.15 (m, 5H), 3.0 (dd, J 7.0, 7.0 Hz, 2H), 2.62 (dd, J
7.0, 7.0 Hz, 2H), 2.30 (s, 3H); 13C NMR (100 MHz, CD3OD): d 144.8,
139.0, 138.4, 130.9, 130.4, 129.0, 128.4, 128.1, 43.3, 38.9, 21.6; HRMS
Compound 115: Rf 0.43 (silica gel, EtOAc/hexanes 1:1); IR (film): nÄmax
1
3383, 1658, 1531, 1428, 1219, 1017, 732 cm 1; H NMR (400 MHz, CDCl3):
d 7.31 (brs, 1H), 7.26 (brs, 1H), 7.16 (dd, J 8.5, 1.5 Hz, 1H), 7.01 (m,
1H), 6.89 (d, J 8.5 Hz, 1H), 6.40 (brs, 1H), 3.87 (s, 2H), 3.68 (q, J
(MALDI-FTMS): calcd for C15H17NO2S3 [M] : 339.0415, found: 339.0416.
Chem. Eur. J. 2001, 7, No. 19
ꢀ WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2001
0947-6539/01/0719-4293 $ 17.50+.50/0
4293