Water → 2-(2-(Tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazole

HRID 74277

反応式

HRID 74277 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.[NH2:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1.O.[H][H]>C(#N)C.[C].[Pd]>[O:23]1[CH2:24][CH2:25][CH2:26][CH:22]1[CH2:21][NH:20][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17]

参加物

7

反応物 4

HCID 962WaterHCID 253298TetrahydrofurfurylamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 674981632-(2-(Tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazole収率 86.2%

試薬・触媒・溶媒 2

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

実験手順

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (0.40 mg, 1.5 mmol) in acetonitrile (8 mL) was added 2-aminomethyltetrahydrofuran (0.36 g, 3.6 mmol), and this was heated to reflux for 7 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 residue obtained in a solvent mixture of methanol/tetrahydrofuran=1:1 (40 mL) was added 10% palladium-carbon (40 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 3 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (0.40 g, 84% yield) as a brown syrup.

後処理

  1. temperaturethis was heated
  2. temperatureto reflux for 7 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the residue obtained in a solvent mixture of methanol/tetrahydrofuran=1:1 (40 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-45b518e81f044c6c87c99006ac06f65a
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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