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Organic & Biomolecular Chemistry
Page 5 of 9
DOI: 10.1039/C7OB01715D
Journal Name
N-(1-Morpholino-1-oxopropan-2-yl)benzamide
ARTICLE
(
8e). The 7.51-7.39 (m, 3H), 7.30 (d, J = 7.9 Hz, 2H), 7.15 (d, J = 7.9 Hz,
crude material was purified by column chromatography using 2H), 5.37 (td, J = 8.5, 5.0 Hz, 1H), 3.91-3.81 (m, 5H), 3.48-3.40
1
PE/EtOAc 4/6 as eluent to give a white solid (85 mg, 65%): H (m, 1H), 3.32-3.23 (m, 2H), 3.14 (dd, J = 13.0, 5.0 Hz, 1H), 3.04
NMR (300 MHz, CDCl3): δ 7.80 (d, J = 7.2 Hz, 2H), 7.48-7.39 (m, (dd, J = 13.0, 5.0 Hz, 1H), 1.63-1.50 (m, 2H), 1.41-1.37 (m, 1H),
3H), 7.34 (br d, J = 6.9 Hz, 1H), 5.06 (quint, J = 6.9 Hz, 1H), 3.71- 1.29 (s, 9H), 0.85-0.76 (m, 1H); 13C NMR (75 MHz, CDCl3): δ
3.66 (m, 6H), 3.59-3.53 (m, 2H), 1.42 (d, J = 6.9 Hz, 3H); 13C 169.8, 166.6, 150.2, 134.1, 133.2, 131.7, 129.4, 128.6, 127.2,
NMR (75 MHz, CDCl3): δ 171.1, 166.4, 134.1, 131.7, 128.6, 125.6, 106.6, 64.4, 50.2, 43.8, 40.3, 39.6, 34.6, 31.4; m/z (ESI):
127.1, 66.8, 66.6, 46.0, 45.5, 42.6, 19.1; m/z (ESI): 263 [M+H]+; 451 [M+H]+; νmax/cm-1 3272, 2962, 2874, 1624, 1541, 1470,
νmax/cm-1 3306, 2902, 2863, 1641, 1534, 1461, 1379, 1109, 1360, 1101, 836, 798, 693; HRMS (ESI) m/z calcd for
965, 844, 718; mp 93.5-94.5 °C; HRMS (ESI) m/z calcd for C27H34N2NaO4 [M+Na]+: 473.2416, found: 473.2411.
C14H19N2O3 [M+H]+: 263.1396, found: 263.1390.
N-(1-(Diethylamino)-1-oxo-3-phenylpropan-2-yl)benzamide
N-(1-Morpholino-3-(4-nitrophenyl)-1-oxopropan-2-
(
8j). The crude material was purified by column
yl)benzamide (8f). The crude material was purified by column chromatography using PE/EtOAc 6/4 as eluent to give a yellow
chromatography using PE/EtOAc 5/5 as eluent to give a yellow solid (99 mg, 61%): 1H NMR (300 MHz, CDCl3): δ 7.78 (d, J = 6.9
1
solid (119 mg, 62%): H NMR (300 MHz, CDCl3, *: referred to Hz, 2H), 7.50-7.40 (m, 3H), 7.29-7.21 (m, 5H), 7.10 (br d, J = 8.0
the main rotamer): δ 8.15 (d, J = 8.7 Hz, 2H)*, 7.75 (d, J = 7.6 Hz, 1H), 5.27 (td, J = 8.0, 6.1 Hz, 1H), 3.57 (dd, J = 13.6, 6.1 Hz,
Hz, 2H), 7.68-7.64 (m, 2H), 7.46-7.36 (m, 3H), 7.11 (br d, J = 7.7 1H), 3.16-3.05 (m, 4H), 3.01 (dd, J = 13.6, 6.1 Hz, 1H), 1.07 (t, J
Hz, 1H), 5.39 (td, J = 7.7, 5.6 Hz, 1H), 3.74-3.70 (m, 4H), 3.65- = 7.2 Hz, 3H), 1.01 (t, J = 7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3):
3.60 (m, 1H), 3.56-3.49 (m, 2H), 3.40-3.32 (m, 1H), 3.30-3.13 δ 170.7, 166.6, 136.5, 134.1, 131.6, 129.7, 128.5 (2C), 127.3,
(m, 2H); 13C NMR (75 MHz, CDCl3, *: referred to the main 127.0, 50.7, 41.9, 40.7, 39.9, 14.3, 12.9; m/z (ESI): 325 [M+H]+;
rotamer): δ 169.3, 166.8*, 147.2*, 144.0*, 140.4*, 133.5, νmax/cm-1 3314, 2984, 2914, 1652, 1628, 1531, 1455, 1364,
130.5*, 128.7*, 127.1*, 123.7*, 66.9*, 66.5*, 49.7, 46.3, 42.6, 1093, 759, 709; mp 98-100 °C; HRMS (ESI) m/z calcd for
38.9; m/z (ESI): 382 [M-H]-; νmax/cm-1 3294, 2976, 1518, 1625, C20H24N2NaO2 [M+Na]+: 347.1735, found: 347.1730.
1438, 1346, 1114, 857, 791; mp 171-172 °C; HRMS (ESI) m/z
calcd for C20H20N3O5 [M-H]-: 382.1403, found: 382.1397.
N-(1-(Benzyl(methyl)amino)-1-oxobutan-2-yl)benzamide
3,4-Dimethoxy-N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-
2-yl)benzamide (8k). The crude material was purified by
column chromatography using PE/EtOAc 4/6 as eluent to give
(
8g). The crude material was purified by column a yellow solid (130 mg, 68%): 1H NMR (300 MHz, CDCl3): δ 7.39
chromatography using PE/EtOAc 7/3 as eluent to give a yellow (s, 1H), 7.33 (d, J = 8.3 Hz, 1H), 7.27-7.23 (m, 5H), 7.04 (br d, J =
1
oil (96 mg, 62%): H NMR (300 MHz, CDCl3, *: referred to the 8.5 Hz, 1H), 6.85 (d, J = 8.3 Hz, 1H), 5.09 (td, J = 8.5, 5.4 Hz,
main rotamer): δ 7.84 (d, J = 7.2 Hz, 2H), 7.50-7.41 (m, 3H), 1H), 3.92 (s, 6H), 3.46-3.30 (m, 3H), 3.07 (dd, J = 12.9, 5.4 Hz,
7.33-7.29 (m, 2H)*, 7.24-7.21 (m, 3H)*, 5.16 (dd, J = 12.6, 7.5 1H), 3.17 (dd, J = 12.9, 5.4 Hz, 1H), 2.65-2.58 (m, 1H), 1.76-1.61
Hz, 1H)*, 4.77 (d, J = 14.7 Hz, 1H), 4.68 (br d, J = 2.6 Hz, 1H), (m, 4H); 13C NMR (75 MHz, CDCl3): δ 170.0, 166.3, 151.9, 148.9,
4.47 (d, J = 14.7 Hz, 1H), 3.05 (s, 3H)*, 1.82-1.67 (m, 2H)*, 1.00 136.6, 129.6, 128.5, 127.1, 126.6, 120.1, 110.6, 110.4, 56.1
(t, J = 7.5 Hz, 3H)*; 13C NMR (75 MHz, CDCl3,*: referred to the (2C), 53.0, 46.5, 45.9, 39.7, 25.8, 24.1; m/z (ESI): 383 [M+H]+;
main rotamer): δ 172.2*, 167.0*, 136.7*, 134.2*, 131.7, νmax/cm-1 3268, 2930, 2880, 1627, 1506, 1454, 1303, 1025,
128.8*, 128.6*, 128.0*,127.2* (2C), 51.4*, 50.7, 34.9*, 26.0*, 863, 760, 702; mp 131-133 °C; HRMS (ESI) m/z calcd for
9.7*; m/z (ESI): 311 [M+H]+; νmax/cm-1 3306, 2969, 2930, 1628, C22H26N2NaO4 [M+Na]+: 405.1790, found: 405.1785.
1578, 1529, 1452, 1354, 802, 695; HRMS (ESI) m/z calcd for
C19H23N2O2 [M+H]+: 311.1760, found: 311.1754.
N-(1-(Isoindolin-2-yl)-1-oxo-3-phenylpropan-2-yl)benzamide
3-Methoxy-N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-
yl)benzamide (8l). The crude material was purified by column
chromatography using PE/EtOAc 5/5 as eluent to give a white
(
8h). The crude material was purified by column solid (134 mg, 76%): 1H NMR (300 MHz, CDCl3): δ 7.39-7.29 (m,
chromatography using PE/EtOAc 7/3 as eluent to give a yellow 1H), 7.29 (d, J = 9.0 Hz, 2H), 7.27-7.23 (m, 5H), 7.12 (br d, J =
1
solid (124 mg, 67%): H NMR (300 MHz, CDCl3): δ 7.80 (d, J = 8.5 Hz, 1H), 7.05-7.01 (m, 1H), 5.09 (td, J = 8.5, 5.4 Hz, 1H),
7.6 Hz, 2H), 7.51-7.38 (m, 3H), 7.29-7.12 (m, 9H), 5.26 (q, J = 3.83 (s, 3H), 3.46-3.30 (m, 3H), 3.16 (dd, J = 12.9, 5.4 Hz, 1H),
7.5 Hz, 1H), 4.99 (d, J = 13.9 Hz, 1H), 4.84 (d, J = 15.9 Hz, 1H), 3.07 (dd, J = 12.9, 5.4 Hz, 1H), 2.66-2.59 (m, 1H), 1.78-1.57 (m,
4.67 (d, J = 15.9 Hz, 1H), 4.16 (d, J = 13.9 Hz, 1H), 3.21 (d, J = 4H); 13C NMR (75 MHz, CDCl3): δ 169.7, 166.6, 159.8, 136.5,
7.5 Hz, 2H); 13C NMR (75 MHz, CDCl3): δ 170.6, 167.0, 136.3, 135.5, 129.6 (2C), 128.5, 127.1, 119.1, 118.1, 112.3, 55.5, 53.0,
136.0, 135.6, 133.9, 131.8, 129.5, 128.6, 128.6, 127.8, 127.7, 46.5, 45.9, 39.7, 25.9, 24.1; m/z (ESI): 353 [M+H]+; νmax/cm-1
127.3, 127.2, 122.9, 122.7, 52.7, 52.4, 52.3, 39.3; m/z (ESI): 371 3256, 2967, 2838, 1615, 1580, 1453, 1365, 1306, 1057, 878,
[M+H]+; νmax/cm-1 3256, 3028, 2868, 1651, 1533, 1352, 1282, 760, 704; mp 163-165 °C; HRMS (ESI) m/z calcd for
758, 704; mp 194-196 °C; HRMS (ESI) m/z calcd for C24H23N2O2 C21H24N2NaO3 [M+Na]+: 375.1685, found: 375.1679.
[M+H]+: 371.1760, found: 371.1754.
N-(1-Oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)-2-
N-(3-(4-(Tert-butyl)phenyl)-1-oxo-1-(1,4-dioxa-8-
naphthamide and N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-
azaspiro[4.5]decan-8-yl)propan-2-yl)benzamide (8i). The crude 2-yl)-1-naphthamide (8m). The crude material was purified by
material was purified by column chromatography using column chromatography using PE/EtOAc 7/3 as eluent to give
PE/EtOAc 7/3 as eluent to give an amorphous yellow solid (119 an inseparable mixture of meta substituted 8m-a and ortho
mg, 53%): 1H NMR (300 MHz, CDCl3): δ 7.78 (d, J = 7.5 Hz, 2H), substituted 8m-b with a ratio meta:ortho 1.3:1, respectively,
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