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Hydrogen Peroxide → 4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)-1H-pyrazole-3-carboxamide

HRID 2361064
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HRID 2361064 반응식
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:37]=[CH:36][C:21]([O:22][C:23]4[C:28]([C:29]5[C:30]([C:34]#[N:35])=[N:31][NH:32][CH:33]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][CH:19]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:39].[K+].[K+].OO>CS(C)=O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([O:22][C:23]4[C:28]([C:29]5[C:30]([C:34]([NH2:35])=[O:39])=[N:31][NH:32][CH:33]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:36][CH:37]=3)=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 178510700HCID 178510700, 화합물

생성물 1

HCID 1361316134-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)-1H-pyrazole-3-carboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
20 °C

실험 절차

In a 20-mL sealed tube was dissolved 4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)-1H-pyrazole-3-carbonitrile (0.070 g, 0.145 mmol) in DMSO (1.0 mL). To this was added potassium carbonate (0.024 g, 0.174 mmol) and hydrogen peroxide (0.445 mL, 14.5 mmol) and the mixture was stirred at 20° C. for 3 days and quenched with water. The product was extracted into EtOAc, washed 1× saturated NaHCO3, 1×H2O, dried over Na2SO4, filtered through fritted funnel and concentrated. The title compound was purified using a Gilson reverse phase liquid chromatography system. The product fractions were extracted into CH2Cl2. The organic layers were washed organics 1× saturated NaHCO3, 1×H2O, dried with Na2SO4, filtered through fritted funnel and concentrated to yield 4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)-1H-pyrazole-3-carboxamide as light yellow solid. MS m/z=500 [M+1]+. Calc'd for C29H21N7O2: 499.52.

후처리

  1. customIn a 20-mL sealed tube
  2. customquenched with water
  3. extractionThe product was extracted into EtOAc
  4. washwashed 1× saturated NaHCO3, 1×H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through fritted funnel
  7. concentrationconcentrated
  8. customThe title compound was purified
  9. extractionThe product fractions were extracted into CH2Cl2
  10. washThe organic layers were washed organics 1× saturated NaHCO3, 1×H2O
  11. dry with materialdried with Na2SO4
  12. filtrationfiltered through fritted funnel
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3e0f8f5b1f954da794d0988ba93d747a
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08686155B2

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