3-Pyridinemethanamine → 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
Reaction equation
FC1C=CC(CN)=CC=1.[NH2:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36](O)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36]([NH:10][CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
4
Procedure
Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 3-(aminomethyl)pyridine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 57% yield: mp 153-154° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.56-8.40 (m, 3H), 7.66 (d, J=7.8 Hz, 1H), 7.35-7.19 (m, 6H), 4.46-4.35 (m, 4H), 3.96 (t, J=7.5 Hz, 2H), 3.41 (t, J=7.5 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.3, 157.8, 155.5, 151.7, 149.3, 148.4, 136.7, 135.6, 135.5, 129.1, 128.2, 127.9, 123.9, 117.9, 47.3, 42.9, 42.4, 40.8, 14.5; MS (ES+) m/z 408.1 (M+1).
Sources & evidence
- ORD record
- ord-0f5a2feb186c4742aa67e1ac2d88f730
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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