Hydrochloric Acid → N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamide

HRID 602001Notes

Reaction equation

HRID 602001 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12](F)=[C:11]([F:16])[CH:10]=1.[CH2:18]([OH:21])[C:19]#[CH:20].[H-].[Na+].Cl>CN(C=O)C>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([O:21][CH2:18][C:19]#[CH:20])=[C:11]([F:16])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 57445707N-(2-methylcyclopentyl)-3,4-difluorobenzamide

Product 1

HCID 57445708N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamideYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2 ml of DMF were added 0.23 g of N-(2-methylcyclopentyl)-3,4-difluorobenzamide and 0.11 g of propargyl alcohol. To the mixture obtained was added 60 mg of 60% sodium hydride (oily) at 0° C. The mixture was stirred at room temperature for 2 hours. Then, dilute hydrochloric acid was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine, dried on magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.11 g of N-(2-methylcyclopentyl)-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 69 of the present invention) represented by the formula:

Workup

  1. customTo the mixture obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bf7884cf91144649307f95aa87047ab
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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