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

HRID 74318

반응식

HRID 74318 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8a848c608a3a4d36982139051f9becb9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

연결된 노트

불러오는 중…