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Hydrogen Peroxide → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(3,4-difluorobenzyl)oxy]nicotinamide

HRID 916979
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HRID 916979 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1.C(O)(C(F)(F)F)=[O:34].[OH-].[K+].OO>O.C(O)C.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:14][C:11]([C:12]([NH2:13])=[O:34])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 443904852-(3,4-Difluorobenzyloxy)-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

생성물 1

HCID 589615746-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(3,4-difluorobenzyl)oxy]nicotinamide

시약·촉매·용매 3

HCID 702
Ethanol
용매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

To the product of Step D Example 129 (30.0 mg, 0.0516 mmol, material in the TFA salt form) was added 1,4-dioxane (4 mL), ethanol (0.5 mL), KOH (0.272 mg, 4.92 mmol), H2O (0.6 mL) and H2O2 (0.21 g). The reaction was heated to 95° C. for 22 hours. The solution was concentrated and the residue was dissolved in ethyl acetate before washing with water, drying (Na2SO4) and concentrating. The residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel) eluting with 10.5% ethyl acetate/dichloromethane affording the product. MS (electrospray) m/e 485.2 MH+ (Rt=4.2 min LC/MS).

후처리

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washbefore washing with water
  4. dry with materialdrying (Na2SO4)
  5. concentrationconcentrating
  6. customThe residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel)
  7. washeluting with 10.5% ethyl acetate/dichloromethane affording the product

출처 및 근거

ORD 기록
ord-94f8fbdd9ca34b1fa4f5ea28b171dd76
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07271266B2

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