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

HRID 74318

反応式

HRID 74318 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a848c608a3a4d36982139051f9becb9
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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