3-Pyridinemethanamine → 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide
Reaction equation
CC1C=C(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)SC=1C(O)=O.[CH3:27][C:28]1[CH:32]=[C:31]([N:33]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]2=[O:46])[S:30][C:29]=1[C:47]([OH:49])=O.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>>[CH3:27][C:28]1[CH:32]=[C:31]([N:33]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]2=[O:46])[S:30][C:29]=1[C:47]([NH:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)=[O:49]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in Example 15, making variations as required to replace 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 3-methyl-5-(2-oxo-3-phenethylimidazolidin-1-yl)thiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 74% yield: mp 95-97° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.52 (d, J=2.2 Hz, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.35-7.18 (m, 6H), 6.12 (t, J=5.6 Hz, 1H), 6.05 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 3.77-3.70 (m, 2H), 3.54 (t, J=7.4 Hz, 2H), 3.46-3.39 (m, 2H), 2.88 (t, J=7.4 Hz, 2H), 2.48 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.6, 155.8, 149.2, 148.8, 142.6, 141.8, 138.4, 135.5, 134.1, 128.6, 126.6, 123.6, 118.7, 112.2, 45.5, 42.8, 42.6, 41.2, 34.1, 16.0; MS (ES+) m/z 421.3 (M+1).
Sources & evidence
- ORD record
- ord-4cf6c8d2bd964a8ab5d2e90ad2686f39
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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