2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione → 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione

HRID 2170812Notes

Reaction equation

HRID 2170812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:27])=[C:11]([CH:13]3[C:17](=[O:18])/[C:16](=[CH:19]/[CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)/[CH2:15][C:14]3=[O:26])[N:12]=2)=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:27])=[C:11]([CH:13]3[C:17](=[O:18])[CH:16]([CH2:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH2:15][C:14]3=[O:26])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 681569242-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 498717052-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dioneYield 23.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (130 mg, 0.32 mmol) in ethanol (2 ml) was added 5% palladium on carbon (13 mg), and the reaction stirred under an atmosphere hydrogen at a pressure of 2 bar for 4 hours. The crude reaction mixture was filtered through a pad of Celite and purified by preparative mass-directed HPLC to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione (30 mg).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through a pad of Celite
  3. custompurified by preparative mass-directed HPLC

Sources & evidence

ORD record
ord-0de296efa06e47eea523b1b21e005017
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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