Hydrochloric Acid → HCID 11440035, compound

HRID 1952868Notes

Reaction equation

HRID 1952868 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([NH:14][C:15]2[S:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][N:19]=2)=[O:13])[N:10]=1)=[O:4].[CH3:23][NH:24][CH3:25].CO.[I-].[K+].Cl>O>[CH3:23][N:24]([CH3:25])[CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][C:12]([NH:14][C:15]2[S:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][N:19]=2)=[O:13])[N:10]=1)=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 887MethanolHCID 4875Potassium IodideHCID 11233675HCID 11233675, compound

Product 1

HCID 11440035HCID 11440035, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-N-(4-{2-[(5-isopropyl-1,3-thiazol-2-yl)amino]-2-oxoethyl}-1,3-thiazol-2-yl)acetamide (0.5 g, 1.4 mmol), 2M dimethylamine in methanol (3.5 ml, 7 mmol) and potassium iodide (0.116 g, 0.7 mmol) was refluxed for about 6 hours. After cooling, the solution was diluted with water, acidified with 1N HCl and extracted with diethyl ether to eliminate the unreacted products. The aqueous solution was then basified with 1N NaOH and extracted with diethyl ether. The organic layer was dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel, using CH2Cl2 :MeOH 97:3 and then 95:5 as eluent. The title compound was obtained in 20% yield (0.1 g) as a light yellow solid.

Workup

  1. temperaturewas refluxed for about 6 hours
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7de04a06a70a4868b85d0ac611188966
Source dataset
uspto-grants-2000_09
Patent number
US06114365

Reaction notes

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