Chloride → HCID 74019988, compound

HRID 1669385Notes

Reaction equation

HRID 1669385 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:26])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:15]=1.[H-].[Na+].[Cl-].[CH2:30]([NH2:33])[C:31]#[CH:32]>CN(C)C=O.O>[CH2:30]([NH:33][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:26])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:15]=1)[C:31]#[CH:32]

Participants

7

Reactant 4

HCID 312ChlorideHCID 24758Sodium hydrideHCID 239041PropargylamineHCID 136344252HCID 136344252, compound

Product 1

HCID 74019988HCID 74019988, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.71 g of 4-hydroxy-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 5 ml of dimethylformamide was added 0.090 g of sodium hydride (60% oily), and this was stirred at room temperature for 1 hour. 0.46 g of paratoluenesulfonyl chloride was added thereto, this was stirred at room temperature for 4 hours, then, 0.60 g of propargylamine was added, and this was stirred at room temperature overnight. To the reaction solution was added water, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 0.080 g of 4-propargylamino-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (13b)] as a yellow crystal.

Workup

  1. stirringthis was stirred at room temperature for 4 hours
  2. stirringthis was stirred at room temperature overnight
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9cd367a8399943be872cc3eb74ce71e3
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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