Potassium Carbonate → 4-((4-(3-((6-Chloro-2-naphthyl)sulfonyl)propanoyl)-1-piperazinyl)methyl)-1,3-thiazol-2-amine

HRID 493697

Reaction equation

HRID 493697 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[CH2:27][C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[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]=[C:30]([NH2:33])[S:31][CH:32]=3)[CH2:23][CH2:24]1)=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 231308831-(3-((6-Chloro-2-naphthyl)sulfonyl)propionyl)piperazine

Product 1

HCID 231309094-((4-(3-((6-Chloro-2-naphthyl)sulfonyl)propanoyl)-1-piperazinyl)methyl)-1,3-thiazol-2-amineYield 71.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-(3-((6-chloro-2-naphthyl)sulfonyl)propionyl)piperazine (1.5 g) obtained in Example 3a), 4-chloromethyl-1,3-thiazol-2-amine hydrochloride (0.76 g) and potassium carbonate (1.12 g) in acetonitrile (50 mL) was refluxed for 4 hours, and then the solvent was distilled off under reduced pressure. The residue was diluted with potassium carbonate, and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with a basic silica gel column to give the title compound (1.4 g) as white crystals.

Workup

  1. temperaturewas refluxed for 4 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with potassium carbonate
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with a basic silica gel column

Sources & evidence

ORD record
ord-88f04dc7c1474d78b2589abb32546252
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Linked notes

Loading…