5-Ethyl-2-thiophenecarboxaldehyde → N-benzyl-2-(3-((5-ethylthiophen-2-yl)methylene)-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 883175Notes

Reaction equation

HRID 883175 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1)[CH3:2].[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[O:31])=[N:22][C:21]=1[CH3:32])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([N:25]2[CH2:30][CH2:29][CH2:28][C:27](=[CH:8][C:6]3[S:7][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)[C:26]2=[O:31])=[N:22][C:21]=1[CH3:32])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1698305-Ethyl-2-thiophenecarboxaldehydeHCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 68497140N-benzyl-2-(3-((5-ethylthiophen-2-yl)methylene)-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamideYield 14%

Procedure

Following the procedure as described in Example 10, making variations as required to use 5-ethylthiophene-2-carbaldehyde 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 14% yield: mp 171-172° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.05 (s, 1H), 7.42-7.22 (m, 5H), 7.16 (d, J=3.7 Hz, 1H), 6.83 (dd, J=0.7, 3.7 Hz, 1H), 5.98 (t, J=5.5 Hz, 1H), 4.57 (d, J=5.5 Hz, 2H), 4.32-4.25 (m, 2H), 2.93-2.81 (m, 4H), 2.65 (s, 3H), 2.15-2.02 (m, 2H), 1.32 (t, J=7.5 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 164.8, 162.7, 157.5, 153.7, 152.4, 137.9, 136.4, 133.6, 132.9, 128.8, 127.9, 127.6, 124.5, 122.7, 119.5, 46.9, 44.1, 25.9, 23.8, 21.9, 17.4, 15.7; MS (ES+) m/z 452.1 (M+1).

Sources & evidence

ORD record
ord-8693b37d5a564350be00b4b843147d0a
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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