Triethylamine → 3,3,3-Trifluoro-N-[4-methyl-2-(pyridin-3-yl)-1,3-thiazol-5-yl]propanamide

HRID 1182778Notes

Reaction equation

HRID 1182778 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[S:5][C:6]=1[NH2:7].C(N(CC)CC)C.[F:21][C:22]([F:28])([F:27])[CH2:23][C:24](Cl)=[O:25]>C1COCC1>[F:21][C:22]([F:28])([F:27])[CH2:23][C:24]([NH:7][C:6]1[S:5][C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:3][C:2]=1[CH3:1])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27833433,3,3-Trifluoropropionyl chlorideHCID 666453454-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine

Product 1

HCID 534829763,3,3-Trifluoro-N-[4-methyl-2-(pyridin-3-yl)-1,3-thiazol-5-yl]propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

286 mg (1.49 mmol) of 4-methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine were dissolved in THF, 0.52 ml of triethylamine was added, and 263 mg of trifluoropropionyl chloride were added while cooling with an ice bath. The mixture was stirred at room temperature overnight and then concentrated. Ethyl acetate, saturated sodium chloride solution and aqueous phosphate buffer pH=7 were added to the residue, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by chromatography (silica gel, cyclohexane, acetone).

Workup

  1. temperaturewhile cooling with an ice bath
  2. concentrationconcentrated
  3. additionEthyl acetate, saturated sodium chloride solution and aqueous phosphate buffer pH=7 were added to the residue
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (silica gel, cyclohexane, acetone)

Sources & evidence

ORD record
ord-2539c85d0839477897a8a5ac17898c13
Source dataset
uspto-grants-2014_03
Patent number
US08664229B2

Reaction notes

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