4-Aminophenol → 4-(3-Morpholinopyridin-2-yloxy)benzenamine

HRID 410184노트

반응식

HRID 410184 반응식
F[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[O:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2]([O:21][C:18]3[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 585476984-(2-Fluoropyridin-3-yl)morpholine

생성물 1

HCID 593272124-(3-Morpholinopyridin-2-yloxy)benzenamine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

To a 25 mL round-bottomed flask were added 4-(2-fluoropyridin-3-yl)morpholine (0.523 g, 2.87 mmol), 4-aminophenol (0.451 g, 2.88 mmol), cesium carbonate (1.18 g, 3.45 mmol) and DMSO (5 mL). The reaction mixture was heated at 120° C. for 8 h. After cooling to room temperature, the reaction mixture was filtered through SCX cartridges, and rinsed with DCM, MeOH, and 2.0 ammonia in MeOH. The ammonia rinses were combined and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40M), eluting with a gradient of 1% to 5% MeOH in CH2Cl2, to provide 4-(3-morpholinopyridin-2-yloxy)benzenamine. MS: [M+1]=272.1

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through SCX cartridges
  3. washrinsed with DCM, MeOH, and 2.0 ammonia in MeOH
  4. concentrationconcentrated
  5. customchromatographed through a Biotage pre-packed silica gel column (40M)
  6. washeluting with a gradient of 1% to 5% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-3ad3bf63cf5f4127afdc176013080045
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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