Pyridine → N-(5-Chloropyridin-2-yl)-5-fluoro-2-(2-acetoxy-4-fluorobenzoylamino)-benzamide

HRID 644281Notes

Reaction equation

HRID 644281 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:18])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].N1C=CC=CC=1.[C:25]([O:28][C:29]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32])(=[O:27])[CH3:26]>C(Cl)Cl>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:17]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[NH:18][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:29]=2[O:28][C:25](=[O:27])[CH3:26])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 210753132-Acetoxy-4-fluorobenzoyl chlorideHCID 219063152-amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

Product 1

HCID 21075344N-(5-Chloropyridin-2-yl)-5-fluoro-2-(2-acetoxy-4-fluorobenzoylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Fluoro-2-amino-N-(5-chloropyridin-2-yl)benzamide (5.32 g, 20 mmol) was added to a solution of 2 mL dry pyridine and 2-acetoxy-4-fluorobenzoyl chloride (21 mmol) in 100 mL dry methylene chloride under dry nitrogen with magnetic stirring. The reaction was allowed to stir overnight at room temperature and then was diluted with 500 mL of methylene chloride. The methylene chloride solution was washed with cold 1 M HCl, cold saturated NaHCO3, and brine; and then was dried over sodium sulfate. The solvent was evaporated, and the crude product was crystallized from acetone to give 2:92 g of off-white product.

Workup

  1. washThe methylene chloride solution was washed with cold 1 M HCl, cold saturated NaHCO3, and brine
  2. dry with materialand then was dried over sodium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was crystallized from acetone
  5. customto give 2

Sources & evidence

ORD record
ord-9c266c90261a465bbd9c8b077d4219b5
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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