976
Vol. 62, No. 10
7.25 (m, 1H,
J
2′–3′=6.4Hz,
J
3′–4′=6.2Hz), 7.43 (m, 1H, (d, 1H, J4′–5′=7.2Hz), 7.26 (m, 1H, J2′–3′=6.4Hz, J3′–4′=6.8Hz),
J2′–4′=1.8Hz,
J
3′–4′=6.4Hz, J4′–5′=6.6Hz), 7.65 (dd, 1H, 7.44 (m, 1H, J2′–4′=1.6Hz, J3′–4′=6.8Hz, J4′–5′=7.2Hz), 7.67
J
2′–4′=1.8Hz, J2′–3′=6.2Hz), 7.96–7.98 (brs, 2H); 13C-NMR (dd, 1H, J2′–4′=1.6Hz, J2′–3′=6.4Hz), 7.86–7.92 (brs, 2H);
(100MHz, CDCl3) δ: 20.9 (1C, CH3–C=O), 24.5 (1C, –CH2– 13C-NMR (100MHz, CDCl3) δ: 13.5 (1C, –(CH2)3–CH3), 18.7
CH2–CH2–), 26.2 (1C, –CH3), 31.3 (1C, –CH2–CH2–CH2–), (1C, –CH2–CH2–CH2–CH3), 20.9 (1C, O=C–CH3), 26.5 (1C,
39.5 (1C, –CH2–CH2–CH2–), 122.9, 126.2, 128.4, 129.2, 131.5, –CH2–CH2–CH2–C=O), 31.1 (1C, –CH2–CH2–CH2–CH3),
147.9 (6C, Ar), 165.9 (1C, –NH–C=O), 169.2 (1C, CH3–C=O), 33.6 (1C, –CH2–CH2–CH2–C=O), 39.5 (1C, –NH–CH2–CH2–
173.6 (1C, –CH2–C(=O)–O); HR-MS(ESI): (M+H+) 279.1391 CH2–), 41.5 (1C, –CH2–CH2–CH2–CH3), 122.5, 125.9, 127.6,
(calculated 279.138), error=2.1 ppm.
128.9, 131.3, 146.8 (6C, Ar), 166.1 (1C, –NH–C=O), 168.9
2-(3-(Ethylcarbamoyl)propylcarbamoyl)phenyl Acetate (2c) (1C, CH3–C=O), 173.1 (1C, –CH2–C(=O)–O); HR-MS(ESI):
4.86g, Yield 67.2%; IR (KBr) ν (cm−1): 3357, 1768, 1734, 1659; (M+H+) 321.1802 (calculated 321.1809), error=2.2ppm.
1H-NMR (400MHz, CDCl3) δ: 1.25 (t, 3H, J=7.2Hz), 1.87 (m,
2-(3-(Diethylcarbamoyl)propylcarbamoyl)phenyl
Acetate
2H, J=6.8Hz, J=7.4Hz), 2.30 (s, 3H), 2.39 (t, 2H, J=7.4Hz), (6c) 4.95g, Yield 58.3%. IR (KBr) ν (cm−1): 3356, 1768,
3.39 (m, 2H, J=6.8Hz), 3.53 (m, 2H, J=7.2Hz), 7.17 (d, 1733, 1660; 1H-NMR (400MHz, CDCl3) δ: 1.11 (m, 6H,
1H, J4′–5′=6.6Hz), 7.25 (m, 1H, J2′–3′=6.2Hz, J3′–4′=6.4Hz), J=7.6Hz), 1.81 (m, 2H, J=6.8Hz), 2.16 (s, 3H), 2.40 (t, 2H,
7.43 (m, 1H, J2′–4′=2.0Hz, J3′–4′=6.4Hz, J4′–5′=6.6Hz), 7.65 J=6.8Hz), 3.39 (q, 2H, J=6.8Hz), 3.42 (m, 4H, J=7.6Hz), 7.10
(dd, 1H, J2′–4′=2.0Hz, J2′–3′=6.2Hz), 7.86–7.98 (brs, 2H); (d, 1H, J4′–5′=6.4Hz), 7.26 (m, 1H, J2′–3′=6.0Hz, J3′–4′=6.4Hz),
13C-NMR (100MHz, CDCl3) δ: 15.5 (1C, –CH2–CH3), 20.7 7.44 (m, 1H, J2′–4′=1.2Hz, J3′–4′=6.4Hz, J4′–5′=6.4Hz), 7.67
(1C, CH3–C=O) 24.2 (1C, –CH2–CH2–CH2–), 31.2 (1C, (dd, 1H, J2′–4′=1.2Hz, J2′–3′=6.0Hz), 7.92 (brs, 2H); 13C-NMR
–CH2–CH2–CH2–), 34.2 (1C, –CH2–CH3), 39.5 (1C, –CH2– (100MHz, CDCl3) δ: 13.8 (2C, –CH2–CH3), 20.5 (1C,O=C–
CH2–CH2–), 123.6, 126.6, 128.6, 129.5, 131.9, 145.8 (6C, Ar), CH3), 26.9 (1C, –CH2–CH2–CH2–C=O), 31.3 (1C, –CH2–
167.8 (1C, –NH–C=O), 169.1 (1C, CH3–C=O, 172.3 (1C,– CH2–CH2–C=O), 39.2 (1C, –NH–CH2–CH2–CH2–), 42.0
CH2–C(=O)–O); HR-MS(ESI): (M+H+) 293.1523 (calculated (2C, –CH2–CH3), 122.3, 125.4, 126.1, 127.8, 131.4, 151.1 (6C,
293.1517), error=2.0ppm.
Ar), 167.5 (1C, –NH–C=O), 168.7 (1C, CH3–C=O), 171.5 (1C,
2-(3-(Isopropylcarbamoyl)propylcarbamoyl)phenyl Acetate –CH2–C(=O)–O); HR-MS(ESI): (M+H+) 321.1819 (calculated
(3c) 5.13g, Yield 61.4%; IR (KBr) ν (cm−1): 3311, 1767, 1734, 321.1809), error=3.1 ppm.
1
1646; H-NMR (400MHz, CDCl3) δ: 1.28 (d, 6H, J=6.8Hz),
2-(3-(Dibutylcarbamoyl)propylcarbamoyl)phenyl
Acetate
1.89 (m, 2H, J=6.8Hz, J=7.4Hz), 2.33 (s, 3H), 2.43 (t, 2H, (7c) 5.26g, Yield 55.6%; IR (KBr) ν (cm−1): 3319, 1767, 1738,
1
J=7.4Hz), 3.33 (m, 2H, J=6.8Hz), 3.88 (m, 1H, J=6.8Hz), 1640; H-NMR (400MHz, CDCl3) δ: 0.95 (t, 6H, J=7.2Hz,
7.01 (d, 1H,
J
4′–5′=6.8Hz), 7.25 (m, 1H,
3′–4′=6.4Hz), 7.45 (m, 1H, 2′–4′=1.2Hz,
4′–5′=6.8Hz), 7.64 (dd, 1H, 2′–4′=1.2Hz,
J
2′–3′=5.2Hz, J=7.6Hz), 1.32 (m, 4H, J=7.2Hz, J=7.6Hz), 1.52 (m, 4H,
J3′–4′=6.4Hz, J=4.6Hz, J=7.6Hz), 1.99 (m, 2H, J=6.4Hz, J=7.2Hz),
J2′–3′=5.2Hz), 2.14 (s, 3H), 2.47 (t, 2H, J=6.4Hz), 3.39 (q, 2H, J=7.2Hz),
J
J
J
J
7.87–7.98 (brs, 2H); 13C-NMR (100MHz, CDCl3) δ: 20.2 (1C, 3.42 (t, 4H, J=4.6Hz), 6.82 (d, 1H, J4′–5′=7.2Hz), 6.87 (m,
CH3–C=O), 23.7 (2C, –CH–(CH3)2), 26.3 (1C, –CH2–CH2– 1H, J2′–3′=6.4Hz, J3′–4′=6.8Hz), 7.47 (m, 1H, J2′–4′=1.0Hz,
CH2–), 32.5 (1C, –CH2–CH2–CH2–), 39.8 (1C, –CH2–CH2–
CH2–), 42.1 (1C, –CH–(CH3)2), 121.1, 124.2, 126.0, 127.2,
J
J
3′–4′=6.8Hz,
J4′–5′=7.2Hz), 7.47 (dd, 1H, J2′–4′=1.0Hz,
2′–3′=6.4Hz), 7.83 (brs, 1H); 13C-NMR (100MHz, CDCl3) δ:
129.5, 146.1 (6C, Ar), 164.2 (1C, –NH–C=O), 168.2 (1C, CH3– 13.7, 13.8 (2C, –CH2–CH2–CH2–CH3), 20.0, 20.1 (2C, –CH2–
C=O), 172.1 (1C, –CH2–C(=O)–O); HR-MS(ESI): M+H+) CH2–CH2–CH3), 21.4 (1C, O=C–CH3), 23.9 (1C, –CH2–CH2–
307.1655 (calculated 307.1652), error=1.0 ppm.
CH2–C=O), 30.4, 30.9 (2C, –CH2–CH2–CH2–CH3), 31.7 (1C,
2-(3-(Propylcarbamoyl)propylcarbamoyl)phenyl Acetate (4c) –CH2–CH2–CH2–C=O), 39.3 (1C, –NH–CH2–CH2–CH2–),
5.02g, Yield 59.3%; IR (KBr) ν (cm−1): 3348, 1773, 1734, 48.0–48.1 (2C, –CH2–CH2–CH2–CH3), 114.3, 118.5, 125.8,
1
1647; H-NMR (400MHz, CDCl3) δ: 0.96 (t, 3H, J=7.2Hz), 127.2, 129.7, 133.9 (6C, Ar), 161.4 (1C, –NH–C=O), 170.0
1.61 (m, 2H, J=7.2Hz), 1.91 (m, 2H, J=6.8Hz, J=7.2Hz), (1C, CH3–C=O), 174.4 (1C, –CH2–C(=O)–O); HR-MS(ESI):
2.23 (s, 3H), 2.40 (t, 2H, J=6.8Hz), 3.40 (m, 2H, J=7.2Hz), (M+H+) 377.2378 (calculated 377.2373), error=1.3 ppm.
3.45 (m, 2H, J=7.2Hz), 6.98 (d, 1H, J4′–5′=6.8Hz), 7.25 (m,
2-(3-(Cyclohexylcarbamoyl)propylcarbamoyl)phenyl Acetate
1H, J2′–3′=6.4Hz, J3′–4′=6.8Hz), 7.43 (m, 1H, J2′–4′=2.0Hz, (8c) 4.86g, Yield 53.7%; IR (KBr) ν (cm−1): 3310, 1767, 1734,
1
J3′–4′=6.8Hz,
J
4′–5′=6.8Hz), 7.69 (dd, 1H,
J
2′–4′=2.0Hz, 1646; H-NMR (400MHz, CDCl3) δ: 1.47 (m, 6H, J=6.8Hz),
J
2′–3′=6.4Hz), 7.96–8.02 (brs, 2H); 13C-NMR (100MHz, 1.82 (m, 2H, J=6.4Hz, J=7.2Hz), 2.08 (s, 3H), 2.41 (t, 2H,
CDCl3) δ: 11.2 (1C, –CH2–CH2–CH3), 20.6 (1C, CH3–C=O), J=6.4Hz), 3.34 (q, 2H, J=7.2Hz), 3.67 (t, 4H, J=6.8Hz), 6.88
23.9 (1C, –CH2–CH2–CH2–), 25.9 (1C, –CH2–CH2–CH2–), (d, 1H, J4′–5′=6.8Hz), 7.05 (m, 1H, J2′–3′=6.4Hz, J3′–4′=6.8Hz),
31.6 (1C, –CH2–CH2–CH2–), 39.8 (1C, –CH2–CH2–CH2–), 7.20 (m, 1H, J2′–4′=1.6Hz, J3′–4′=6.8Hz, J4′–5′=6.8Hz), 7.43
41.5 (1C, –CH2–CH2–CH3), 122.9, 126.3, 128.2 129.9, (dd, 1H, J2′–4′=1.6Hz, J2′–3′=6.4Hz), 7.78 (brs, 1H); 13C-NMR
131.5147.5 (6C, Ar), 165.6 (1C, –NH–C=O), 169.1 (1C, CH3– (100MHz, CDCl3) δ: 20.1 (1CO=C–CH3), 25.2 (1C, –(CH2)2–
C=O), 173.1 (1C, –CH2–C(=O)–O); HR-MS(ESI): M+H+) CH2–(CH2)2–), 25.9 (1C, –CH2–CH2–CH2–C=O), 28.2–28.3
307.16 (calculated 307.1652), error=1.6 ppm.
(2C, –CH2–CH2–CH2–CH2–CH2–), 31.7 (1C, –CH2–CH2–
2-(3-(Butylcarbamoyl)propylcarbamoyl)phenyl Acetate (5c) CH2–C=O), 6.9 (1C, –NH–CH2–CH2–CH2–), 41.8–41.9 (2C,
5.28g, Yield 61.2%; IR (KBr) ν (cm−1): 3281, 1765, 1648; –CH2–(CH2)3–CH2–), 114.8, 119.3, 125.8, 127.3, 129.6, 133.9
1H-NMR (400MHz, CDCl3) δ: 0.92 (t, 3H, J=6.0Hz), 1.32 (m, (6C, Ar), 161.3 (1C, –NH–C=O), 170.2 (1C, CH3–C=O), 173.9
2H, J=6.0Hz, J=6.2Hz), 1.64 (m, 2H, J=5.8Hz, J=6.2Hz), (1C, –CH2–C(=O)–O). HR-MS(ESI): (M+H+) 333.1798 (cal-
1.93 (q, 2H, J=6.4Hz, J=7.2Hz), 2.28 (s, 3H), 2.41 (t, 2H, culated 333.1792), error=1.8 ppm.
J=6.4Hz), 3.39 (q, 2H, J=7.2Hz), 3.41 (t, 1H, J=5.8Hz), 7.08
2-(3-(Methylpyrazinecarbamoyl)propylcarbamoyl)phenyl