Phenylacetaldehyde → N-benzyl-4-methyl-2-(2-oxo-3-phenethylpiperidin-1-yl)thiazole-5-carboxamide

HRID 883159Notes

Reaction equation

[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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][CH:27]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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

Reactant 2

HCID 998Phenylacetaldehyde

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

Product 1

HCID 24801325N-benzyl-4-methyl-2-(2-oxo-3-phenethylpiperidin-1-yl)thiazole-5-carboxamideYield 24%

Procedure

Following the procedure as described in Example 3, making variations as required to use 2-phenylacetaldehyde in place of cyclopropanecarbaldehyde to react with N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 24% yield: mp 124-126° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.46-7.09 (m, 10H), 5.98 (t, J=5.4 Hz, 1H), 4.55 (d, J=5.4 Hz, 2H), 4.29-4.20 (m, 1H), 4.07-4.04 (m, 1H), 2.83-2.66 (m, 2H), 2.64 (s, 3H), 2.61-2.48 (m, 1H), 2.41-2.26 (m, 1H), 2.17-2.01 (m, 2H), 1.96-1.76 (m, 2H), 1.74-1.58 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 172.8, 162.7, 156.9, 152.2, 141.3, 137.9, 128.8, 128.5, 128.4, 127.9, 127.6, 126.1, 119.1, 47.9, 44.1, 41.4, 33.3, 33.0, 25.7, 21.3, 17.4; MS (ES+) m/z 434.1 (M+1).

Sources & evidence

ORD record: ord-41aa276acc154bbaadae16a0db9ccbf5
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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