N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide → N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide

HRID 1892516Notes

Reaction equation

HRID 1892516 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:10][C:9]([CH:11]=[CH:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:8][C:7]=1[CH3:22]>C(OCC)(=O)C.C(O)(=O)C.[C].[Pd]>[CH:2]([C:6]1[S:10][C:9]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:8][C:7]=1[CH3:22])=[O:1]

Participants

5

Reactant 1

HCID 86650016N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 86650017N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamideYield 58.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-{2-[5-(1,3-Dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (4.42 g, 13.1 mmol) was dissolved in a mixture of ethyl acetate (400 ml) and acetic acid (100 ml), and 10% palladium carbon (2.21 g, containing 50% water) was added. The mixture was hydrogenated at room temperature under an atmospheric pressure. The reaction mixture was filtered through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6) to give N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide (2.26 g, 7.68 mmol, yield 58.4%) as a yellow solid.

Workup

  1. additionwas added
  2. customwas hydrogenated at room temperature under an atmospheric pressure
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6)

Sources & evidence

ORD record
ord-af395db415e947988f5386a1e457729b
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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