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

HRID 523452Notes

Reaction equation

HRID 523452 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-02aba1381fe9413e960d5337e11df2c6
Source dataset
uspto-grants-2016_05
Patent number
US09339032B2

Reaction notes

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