Triethylamine → 5-Chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole

HRID 74318Notes

Reaction equation

HRID 74318 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13](F)=[C:14]([N+:16]([O-])=O)[CH:15]=3)=[N:7][C:6]=2[CH:20]=1.C(N(CC)CC)C.Cl.[F:29][C:30]([F:35])([F:34])[CH2:31][CH2:32][NH2:33].[H][H]>C(#N)C.[C].[Pd].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:33][CH2:32][CH2:31][C:30]([F:35])([F:34])[F:29])=[C:14]([CH:15]=3)[NH2:16])=[N:7][C:6]=2[CH:20]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 252105053,3,3-Trifluoropropylamine hydrochlorideHCID 674975535-Chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674982645-Chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazoleYield 100%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazole (see Working Example 100-1) (815 mg, 2.79 mmol) in acetonitrile (10 mL) was added triethylamine (847 mg, 8.37 mmol) and 3,3,3-trifluoropropylamine hydrochloride (500 mg, 3.34 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL) was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 18 hours. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (993 mg, 100% yield) as orange crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8a848c608a3a4d36982139051f9becb9
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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