3-Pyridinecarboxaldehyde → N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethylene)piperidin-1-yl)thiazole-5-carboxamide

HRID 883176Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]2=[O:30])=[N:21][C:20]=1[CH3:31])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C:26](=[CH:1][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[C:25]2=[O:30])=[N:21][C:20]=1[CH3:31])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 103713-Pyridinecarboxaldehyde

HCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 68492245N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethylene)piperidin-1-yl)thiazole-5-carboxamideYield 17%

Procedure

Following the procedure as described in Example 10, making variations as required to use nicotinaldehyde in place of benzaldehyde to react with N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 17% yield: mp 206-208° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.69 (br s, 1H), 8.54 (br s, 1H), 7.91 (s, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.39-7.21 (m, 6H), 6.26 (t, J=5.5 Hz, 1H), 4.57 (d, J=5.5 Hz, 2H), 4.32-4.22 (m, 2H), 2.93-2.82 (m, 2H), 2.64 (s, 3H), 2.09-1.96 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 163.8, 162.6, 157.3, 152.3, 150.7, 149.4, 138.0, 136.8, 135.5, 130.5, 128.8, 127.9, 127.6, 123.5, 120.1, 47.4, 44.0, 25.9, 22.2, 17.4; MS (ES+) m/z 419.2 (M+1).

Sources & evidence

ORD record: ord-6119742d26884e01b2e19ff7ae09903e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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