Water → 5-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole

HRID 74283노트

반응식

HRID 74283 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.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.O.[H][H]>C(#N)C.[C].[Pd]>[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:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:14]([CH:15]=3)[NH2:16])=[N:7][C:6]=2[CH:20]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 4192234-AminotetrahydropyranHCID 674975535-Chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole수율 49%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

To a suspension of 5-chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazole (see Working Example 100-1) (5.00 g, 17.1 mmol) in acetonitrile (20 mL) was added 4-aminotetrahydropyran (3.81 g, 38.0 mmol), and this was heated to reflux for 3 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 a solvent mixture of methanol/tetrahydrofuran (1:1, 100 mL) was added 10% palladium-carbon (500 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature overnight. After the reaction was complete, this was filtered through Celite, the filtrate was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (2.86 g, 49% yield) as yellowish-brown crystals.

후처리

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the crystals obtained in a solvent mixture of methanol/tetrahydrofuran (1:1, 100 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-5316f5fc15264fd8ac7f4d857b88507c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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