Chemical Papers
Table 2 1H NMR, MS, and elemental analysis data of compounds 9a–r
Comp 1H NMR (δ); MS (m/e); elemental analysis
9a
9b
9c
9d
9e
9f
1H NMR (CDCl3) δ: 2.45 (s, 3H, CH3), 2.53 (s, 3H, CH3), 4.67 (dd, J=5.7, 0.9 Hz, 2H, CH2), 5.90 (br, 1H, NH), 7.45–7.49 (m, 3H,
Ph H), 7.67 (t, J=0.9 Hz, 1H, oxzole H), 8.02–8.05 (m, 2H, Ph H); GC–MS M+ =314; Calcd: C, 61.05; H, 4.80; N, 17.80, found: C,
61.02; H, 4.83; N, 17.82
1H NMR (CDCl3) δ: 2.43 (s, 3H, CH3), 2.52 (s, 3H, CH3), 4.70 (dd, J=5.7, 0.9 Hz, 2H, CH2), 5.87 (br, 1H, NH), 7.33–7.42 (m, 2H, Ph
H), 7.48–7.52 (m, 1H, Ph H), 7.74 (t, J=0.9 Hz, 1H, oxazole H), 7.95–7.98 (m, 1H, Ph H); GC–MS M+ =348; Calcd: C, 55.03; H,
4.04; N, 16.04, found: C, 55.02; H, 4.07; N, 16.08
1H NMR (CDCl3) δ: 2.46 (s, 3H, CH3), 2.54 (s, 3H, CH3), 4.70 (dd, J=5.7, 0.9 Hz, 2H, CH2), 5.92 (br, 1H, NH), 7.35 (q, J=5.7, 1H,
Ph H), 7.53 (d, J=2.1, 1H, Ph H), 7.74 (d, J=0.9 Hz, 1H, oxazole H), 7.94 (d, J=8.4 Hz, 1H, Ph H); HPLC–MS Pos [M+1]+ =385;
Calcd: C, 50.09; H, 3.42; N, 14.60, found: C, 50.03; H, 3.46; N, 14.63
1H NMR (CDCl3) δ: 2.44 (s, 3H, CH3), 2.53 (s, 3H, CH3), 2.68 (s, 3H, CH3), 4.68 (dd, J=5.4, 0.9 Hz, 2H, CH2), 5.91 (br, 1H, NH),
7.28–7.37 (m, 3H, Ph H), 7.68 (t, J=0.9 Hz, 1H, oxazole H), 7.95–7.98 (m, 1H, Ph H); HPLC–MS Pos [M+1]+ =329; Calcd: C,
62.10; H, 5.21; N, 17.04, found: C, 62.08; H, 5.23; N, 17.10
1H NMR (CDCl3) δ: 2.42 (s, 3H, CH3), 2.43 (s, 3H, CH3), 2.51 (s, 3H, CH3), 4.66 (dd, J=5.7, 0.9 Hz, 2H, CH2), 5.83 (br, 1H, NH),
7.27–7.37 (m, 2H, Ph H), 7.64 (d, J=0.9 Hz, 1H, oxazole H), 7.80–7.86 (m, 2H, Ph H); GC–MS M+ =328; Calcd: C, 62.10; H, 5.21;
N, 17.04, found: C, 62.04; H, 5.23; N, 17.11
1H NMR (CDCl3) δ: 2.41 (s, 3H, CH3), 2.44 (s, 3H, CH3), 2.52 (s, 3H, CH3), 4.66 (dd, J=5.4, 0.9 Hz, 2H, CH2), 5.86 (br, 1H, NH),
7.25–7.28 (m, 2H, Ph H), 7.63 (t, J=1.2 Hz, 1H, oxazole H), 7.90–7.93 (m, 2H, Ph H); HPLC–MS Pos [M+1]+ =329; Calcd: C,
62.10; H, 5.21; N, 17.04, found: C, 62.05; H, 5.23; N, 17.11
9g
9h
9i
1H NMR (CDCl3) δ: 2.36 (s, 3H, CH3), 2.44 (s, 3H, CH3), 2.52 (s, 3H, CH3), 2.64 (s, 3H, CH3), 4.67(dd, J=5.4, 1.2 Hz, 2H, CH2), 5.89
(br, 1H, NH), 7.08–7.10 (m, 2H, Ph H), 7.65 (t, J=0.9 Hz, 1H, oxazole H), 7.85 (d, J=8.4, 1H, Ph H); GC–MS M+ =342; Calcd: C,
63.06; H, 5.59; N, 16.34, found: C, 63.03; H, 5.63; N, 16.40
1H NMR (CDCl3) δ: 1.24–1.34(m, 5H, CH2CH3, 2.43 (s, 3H, CH3), 2.51 (s, 3H, CH3), 4.65 (dd, J=5.7, 0.4 Hz, 2H, CH2), 5.85 (br,
1H, NH), 7.27 (d, J=8.1 Hz, 2H, Ph H), 7.66 (t, J=0.9 Hz, 1H, oxazole H), 7.92 (dd, J=6.6, 1.6 Hz, 2H, Ph H); GC–MS M+ =342;
Calcd: C, 63.06; H, 5.59; N, 16.34, found: C, 63.01; H, 5.66; N, 16.41
1H NMR (CDCl3) δ: 2.44 (s, 3H, CH3), 2.52 (s, 3H, CH3), 4.68 (dd, J=5.7, 0.9 Hz, 2H, CH2), 5.84 (br, 1H, NH), 7.71 (dd, J=8.4,
0.9 Hz, 2H, Ph H), 7.72 (d, J=0.9 Hz, 1H, oxazole H), 8.13 (dd, J=8.4, 0.6 Hz, 2H, Ph H); HPLC–MS Pos [M+1]+ =383; Calcd: C,
53.34; H, 3.69; N, 14.64, found: C, 53.31; H, 3.72; N, 14.71
9j
1H NMR (CDCl3) δ: 1.24 (t, J=7.5 Hz, 3H, CH3), 2.52 (s, 3H, CH3), 2.76 (q, J=7.5 Hz, 2H, CH2), 4.67 (dd, J=5.7, 0.9 Hz, 2H, CH2),
5.85 (br, 1H, NH), 7.44–7.48 (m, 3H, Ph H), 7.66 (s, 1H, oxazole H), 8.02–8.05 (m, 2H, Ph H); GC–MS M+ =328; Calcd: C, 62.10; H,
5.21; N, 17.04, found: C, 62.05; H, 5.28; N, 17.07
9k
9l
1H NMR (CDCl3) δ: 1.24 (t, J=7.5 Hz, 3H, CH3), 2.53 (s, 3H, CH3), 2.76 (q, 7.5 Hz, 2H, CH2), 4.70 (dd, J=5.4, 0.9 Hz, 2H, CH2),
5.88 (br, 1H, NH), 7.35–7.42 (m, 2H, Ph H), 7.49–7.53 (m, 1H, Ph H), 7.75 (t, J=0.9 Hz, 1H, oxazole H), 7.96–7.99 (m, 1H, Ph H);
GC–MS M+ =362; Calcd: C, 56.21; H, 4.44; N, 15.42, found: C, 56.15; H, 4.50; N, 15.43
1H NMR (CDCl3) δ: 1.26 (t, J=7.5 Hz, 3H, CH3), 2.52 (s, 3H, CH3), 2.76 (q, J=7.5 Hz, 2H, CH2), 4.69 (dd, J=5.7, 0.9 Hz, 2H, CH2),
5.87 (br, 1H, NH), 7.74 (t, J=0.9 Hz, 1H, oxazole H), 7.33–7.95 (m, 3H, Ph H); HPLC–MS Pos [M+1]+ =399; Calcd: C, 51.34; H,
3.80; N, 14.09, found: C, 51.32; H, 3.82; N, 14.13
9m
9n
9o
9p
1H NMR (CDCl3) δ: 1.22 (t, J=7.5 Hz, 3H, CH3), 2.53 (s, 3H, CH3), 2.67 (s, 3H, CH3), 2.77 (q, J=7.5 Hz, 2H, CH2), 4.88 (dd, J=5.4,
1.2 Hz, 2H, CH2), 5.92 (br, 1H, NH), 7.68 (t, J=0.9 Hz, 1H, oxazole H), 7.28–7.98 (m, 4H, Ph H); HPLC–MS Pos [M+1]+ =343;
Calcd: C, 63.06; H, 5.59; N, 16.34, found: C, 63.02; H, 5.63; N, 16.45
1H NMR (CDCl3) δ: 1.25 (t, J=7.5 Hz, 3H, CH3), 2.42 (s, 3H, CH3), 2.53 (s, 3H, CH3), 2.75 (q, J=7.5 Hz, 2H, CH2), 4.66 (dd, J=5.4,
0.6 Hz, 2H, CH2), 5.86 (br, 1H, NH), 7.65 (t, J=0.9 Hz, 1H, oxazole H), 7.28–7.87 (m, 4H, Ph H); GC–MS M+ =342; Calcd: C,
63.06; H, 5.59; N, 16.34, found: C, 63.05; H, 5.67; N, 16.45
1H NMR (CDCl3) δ: 1.24 (t, J=7.5 Hz, 3H, CH3), 2.40 (s, 3H, CH3), 2.52 (s, 3H, CH3), 2.76 (q, J=7.5 Hz, 2H, CH2), 4.66 (dd, J=5.4,
0.9 Hz, 2H, CH2), 5.86 (br, 1H, NH), 7.27 (d, J=4.5 Hz, 2H, Ph H), 7.63 (t, J=0.9 Hz, 1H, oxazole H), 7.90–7.93 (m, 2H, Ph H);
HPLC–MS Pos [M+1]+ =343; Calcd: C, 63.06; H, 5.59; N, 16.34, found: C, 63.04; H, 5.69; N, 16.37
1H NMR (DMSO-d6) δ: 1.15 (t, J=7.5 Hz, 3H, CH3), 2.31 (s, 3H, CH3), 2.36 (s, 3H, CH3), 2.57 (s, 3H, CH3), 2.65 (q, J=7.5 Hz,2H,
CH2), 4.53 (dd, J=5.1, 0.9 Hz, 2H, CH2), 5.76 (br, 1H, NH), 7.12–7.17 (m, 1H, Ph H), 7.57 (t, J=5.7 Hz, 1H, Ph H), 7.77 (d,
J=7.8 Hz, 1H, Ph H), 7.94 (s, 1H, oxazole H); GC–MS M+ =356; Calcd: C, 63.95; H, 5.93; N, 15.70, found: C, 63.87; H, 5.95; N,
15.81
9q
9r
1H NMR (CDCl3) δ: 1.21–1.34 (m, 6H, CH3), 2.52 (s, 3H, CH3), 2.69–2.79 (m, 4H, CH3), 4.65 (d, J=5.4 Hz, 2H, CH2), 5.85 (br, 1H,
NH), 7.27 (d, J=8.1 Hz, 2H, Ph H), 7.63 (s, 1H, oxazole H), 7.93 (m, 2H, Ph H); GC–MS M+ =356; Calcd: C, 63.95; H, 5.93; N,
15.70, found: C, 63.89; H, 5.97; N, 15.85
1H NMR (CDCl3) δ: 1.24 (t, J=7.5 Hz, 3H, CH3), 2.52 (s, 3H, CH3), 2.72 (q, J=7.5 Hz, 2H, CH2), 4.68 (dd, J=5.7, 0.9 Hz, 2H, CH2),
5.84 (br, 1H, NH), 7.71 (s, 1H, oxazole H), 7.72–7.74 (m, 2H, Ph H), 8.13 (d, J=8.1 Hz, 2H, Ph H); HPLC–MS Pos [M+1]+ =396;
Calcd: C, 54.49; H, 4.06; N, 14.36, found: C, 54.42; H, 4.22; N, 14.41
1 3