2,4-Dichloropyrimidine → 2-{4-[1-(2-Chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

HRID 409730Notes

Reaction equation

HRID 409730 reaction equation
[CH2:1]([NH:3][C:4](=[O:19])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[Cl:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[CH:23][N:22]=1>CN(C=O)C>[Cl:20][C:21]1[N:26]=[C:25]([N:16]2[CH2:17][CH2:18][CH:13]([C:10]3[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([NH:3][CH2:1][CH3:2])=[O:19])=[CH:8][CH:9]=3)[CH2:14][CH2:15]2)[CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 86686109N-Ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide

Product 1

HCID 866861182-{4-[1-(2-Chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

355 μL (2.53 mmol) TEA are added to a mixture of 600 mg (2.30 mmol) N-ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide (VI.1) and 377 mg (2.53 mmol) 2,4-dichloro-pyrimidine in 25 mL DMF. The mixture is stirred for 3 h at rt. Subsequently the solvent is removed in vacuo and the residue is purified using reversed phase HPLC (water, 0.3% NH4OAc/acetone) to yield the desired product.

Workup

  1. customSubsequently the solvent is removed in vacuo
  2. customthe residue is purified

Sources & evidence

ORD record
ord-738dd25c52044037a75867ab86262077
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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