3-Pyridinemethanamine → 3-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide
Reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[CH3:25][C:26]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][N:33]([CH2:36][C:37](=[O:44])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]2=[O:45])[S:28][C:27]=1[C:46]([OH:48])=O.[NH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>>[CH3:25][C:26]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][N:33]([CH2:36][C:37](=[O:44])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]2=[O:45])[S:28][C:27]=1[C:46]([NH:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)=[O:48]Participants
Reactant 3
Product 1
Procedure
Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 3-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a cream solid in 61% yield: mp 174-176° C.: 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.48 (d, J=4.4 Hz, 1H), 7.97-7.92 (m, 2H), 7.67 (d, J=7.8 Hz, 1H), 7.64-7.57 (m, 1H), 7.51-7.44 (m, 2H), 7.23 (dd, J=7.8, 4.4 Hz, 1H), 6.24 (t, J=5.7 Hz, 1H), 6.11 (s, 1H), 4.72 (s, 2H), 4.56 (d, J=5.7 Hz, 2H), 3.93-3.85 (m, 2H), 3.75-3.67 (m, 2H), 2.48 (s, 3H): 13C NMR (75 MHz, CDCl3) δ 193.8, 163.5, 156.2, 149.2, 148.7, 142.4, 141.6, 135.5, 134.6, 134.2, 134.0, 128.9, 127.9, 123.5, 112.6, 50.0, 43.0, 42.7, 41.1, 16.1: MS (ES+) m/z 435.4 (M+1).
Sources & evidence
- ORD record
- ord-2bd6f5e28c2f4f2d9f3ddfaff9ab70b4
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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