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

HRID 883177Notes

Reaction equation

HRID 883177 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C:18](=[CH:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]2=[O:29])=[N:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH:18]([CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]2=[O:29])=[N:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 24801324N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethyl)piperidin-1-yl)thiazole-5-carboxamideYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethylene)piperidin-1-yl)thiazole-5-carboxamide (0.024 g, 0.053 mmol) in ethyl acetate (10 mL) was hydrogenated in the presence of catalytic amount of palladium on carbon (20% w/w) at ambient temperature and under atmospheric pressure for 3 hours. The reaction mixture was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was recrystallized from hexanes/ethyl acetate to afford the title compound as a yellow solid (0.022 g, 92%): mp 140-141° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.44 (br s, 2H), 7.51 (d, J=7.8 Hz, 1H), 7.42-7.16 (m, 6H), 6.07 (br s, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.33-4.21 (m, 1H), 3.98-3.86 (m, 1H), 3.43-3.29 (m, 1H), 3.91-3.73 (m, 2H), 2.62 (s, 3H), 2.11-2.98 (m, 1H), 1.96-1.74 (m, 2H), 1.62-1.45 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.5, 162.6, 156.8, 152.1, 150.4, 147.9, 137.9, 136.9, 128.8, 128.7, 127.9, 127.6, 123.6, 119.6, 47.9, 44.1, 43.8, 34.6, 24.9, 21.3, 17.4; MS (ES+) m/z 421.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-1bae3d87d12e4f4380530100aeea3e47
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

Loading…