Propargyl alcohol → N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-difluorobenzamide

HRID 601990Notes

Reaction equation

HRID 601990 reaction equation
[CH:1]1([CH2:7][NH:8][C:9](=[O:19])[C:10]2[CH:15]=[C:14]([F:16])[C:13](F)=[C:12]([F:18])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:20]([OH:23])[C:21]#[CH:22].[H-].[Na+]>CN(C=O)C>[CH:1]1([CH2:7][NH:8][C:9](=[O:19])[C:10]2[CH:11]=[C:12]([F:18])[C:13]([O:23][CH2:20][C:21]#[CH:22])=[C:14]([F:16])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 57445689N-cyclohexylmethyl-3,4,5-trifluorobenzamide

Product 1

HCID 57445690N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-difluorobenzamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 ml of DMF were added 0.50 g of N-cyclohexylmethyl-3,4,5-trifluorobenzamide and 0.15 g of propargyl alcohol and to the mixture obtained was added 100 mg of sodium hydride at 0° C. The mixture obtained was stirred at room temperature for 2 hours. Then, the reaction mixture was concentrated. The residue was subjected to silica gel column chromatography to obtain 0.49 g of N-cyclohexylmethyl-4-(2-propynyloxy)-3,5-difluorobenzamide (hereinafter, described as the compound 32 of the present invention) represented by the formula:

Workup

  1. customto the mixture obtained
  2. customThe mixture obtained
  3. concentrationThen, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-654479aa1bb64bec9802d847b74d6aaa
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

Loading…