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

HRID 74277

반응식

HRID 74277 반응식
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]

참가 물질

7

반응물 4

HCID 962WaterHCID 253298TetrahydrofurfurylamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45b518e81f044c6c87c99006ac06f65a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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