Hydrochloric Acid → HCID 178482540, compound

HRID 493695

Reaction equation

HRID 493695 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2.Cl.[Cl:26][CH2:27][C:28]1[N:29]([CH3:35])/[C:30](=[N:33]/[CH3:34])/[S:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(OCC)(=O)C.CCOCC>[ClH:1].[ClH:26].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:19]1[CH2:20][CH2:21][N:22]([CH2:27][C:28]3[N:29]([CH3:35])/[C:30](=[N:33]/[CH3:34])/[S:31][CH:32]=3)[CH2:23][CH2:24]1)=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 231308831-(3-((6-Chloro-2-naphthyl)sulfonyl)propionyl)piperazineHCID 178482537HCID 178482537, compound

Product 1

HCID 178482540HCID 178482540, compoundYield 121.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-(3-((6-chloro-2-naphthyl)sulfonyl)propionyl)piperazine (2.5 g) obtained in Example 3a), N-((2Z)-4-chloromethyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-N-methylamine hydrochloride (2.2 g) and potassium carbonate (2.4 g) in DMF (50 mL) was mixed at 65° C. for 3 hours. The solvent was distilled off under reduced pressure, the residue was diluted with an aqueous potassium carbonate solution, and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The product, which was obtained by the purification of the residue with a basic silica gel column, was dissolved in ethyl acetate. A solution of hydrogen chloride in ether was added thereto, and the mixture was concentrated and dried to give the title compound (2.4 g) as a colorless powder.

Workup

  1. additionwas mixed at 65° C. for 3 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with an aqueous potassium carbonate solution
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product, which was obtained by the purification of the residue with a basic silica gel column
  8. concentrationthe mixture was concentrated
  9. customdried

Sources & evidence

ORD record
ord-3a3fbf0254c84df7ae80a04ae775c56e
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Linked notes

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