Potassium Carbonate → 1-(4-{2-[2-Oxo-4-(thiophen-2-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidine-4-carboxylic Acid Dimethylamide

HRID 564157Notes

Reaction equation

HRID 564157 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]3=[O:27])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].Br[CH2:30][C:31]1[S:32][CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:28][N:2]([CH3:1])[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:30][C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)=[CH:22][C:21]3=[O:27])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118299782-(Bromomethyl)thiopheneHCID 670074151-{4-[2-(4-Hydroxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-piperidine-4-carboxylic Acid Dimethylamide

Product 1

HCID 580428531-(4-{2-[2-Oxo-4-(thiophen-2-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidine-4-carboxylic Acid Dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 mg (0.13 mmol) 1-{4-[2-(4-hydroxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-piperidine-4-carboxylic acid dimethylamide (example 17.1a) in 2.0 mL DMF is added 130 μL (1 M solution in 1,4-dioxane, 0.13 mmol) 2-bromomethyl-thiophene and 45 mg (0.33 mmol) potassium carbonate at 0° C. The reaction mixture is stirred overnight at RT, filtered and the solvent is evaporated. The residue is dissolved in 2.5 mL of DMF and is purified via reverse HPLC chromatography (Waters symmetry, C18, 7 μm; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

Workup

  1. filtrationfiltered
  2. customthe solvent is evaporated
  3. dissolutionThe residue is dissolved in 2.5 mL of DMF
  4. customis purified via reverse HPLC chromatography (Waters symmetry, C18, 7 μm; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Sources & evidence

ORD record
ord-1885383fbead492abdbfcc71ab7f9ea1
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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