Potassium Carbonate → 4-(5-Chloropyridin-2-yloxy)-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]benzamide

HRID 2426688Notes

Reaction equation

HRID 2426688 reaction equation
[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:4]1.Cl[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([O:22][C:19]2[CH:18]=[CH:17][C:16]([C:15]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:6][CH2:7][CH:3]([N:2]([CH3:24])[CH3:1])[CH2:4]4)=[CH:13][CH:12]=3)=[O:23])=[CH:21][CH:20]=2)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 276852,5-DichloropyridineHCID 21105609N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]-4-hydroxybenzamide

Product 1

HCID 211054664-(5-Chloropyridin-2-yloxy)-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.05 g of N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]-4-hydroxybenzamide, 0.017 g of 2,5-dichloropyridine and 0.064 g of potassium carbonate in 0.8 ml of DMF was heated at 230° C. in a microwave apparatus for 30 minutes. The solution was filtered and purified by preparative HPLC. This resulted in the product with the molecular weight of 436.17 (C24H25CIN4O2); MS (ESI): 437 (M+H+) as hydrotrifluoroacetate.

Workup

  1. filtrationThe solution was filtered
  2. custompurified by preparative HPLC
  3. customThis resulted in the product with the molecular weight of 436.17 (C24H25CIN4O2)

Sources & evidence

ORD record
ord-46bfdc27c9954a1dabcf5cdc7928fb91
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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