2-Aminothiazole → HCID 22288379, compound

HRID 968325Notes

Reaction equation

HRID 968325 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([C:11]2[S:15][C:14]([C:16](Cl)=[O:17])=[CH:13][CH:12]=2)=[N:3]1.ClCCl.[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C(=O)(O)[O-].[Na+]>O>[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([C:11]2[S:15][C:14]([C:16]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:17])=[CH:13][CH:12]=2)=[N:3]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6344Dichloromethane2×HCID 516892Sodium BicarbonateHCID 22288389HCID 22288389, compound

Product 1

HCID 22288379HCID 22288379, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1-Methyl-5-trifluoromethyl-1H-pyrazol-3-yl)thiophene-2-carbonyl chloride (100 mg) and dichloromethane (2 ml) were added to a mixture of 2-aminothiazole (68 mg), saturated sodium bicarbonate aqueous solution (1 ml) and dichloromethane (1 ml), followed by stirring at room temperature for 5 hours. Water was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1-2:1) and then washed with diethyl ether to give 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-N-(2-thiazolyl)thiophene-2-carboxamide (68 mg) as colorless solid.

Workup

  1. extractionthe thus formed product was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1-2:1)
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-45083af65b9b4c95bccbfcda438c3940
Source dataset
uspto-grants-2005_10
Patent number
US06958339B2

Reaction notes

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