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Ethylene Glycol → 2-(2-(5-fluoropyridin-2-yl)-1,3-dioxolan-2-yl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine

HRID 473174
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HRID 473174 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[O:9])=[N:6][CH:7]=1.[CH2:27](O)[CH2:28][OH:29].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:10]3[N:19]=[C:18]([NH:20][C:21]4[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=4)[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=3)[O:29][CH2:28][CH2:27][O:9]2)=[N:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 56848496(5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone

생성물 1

HCID 666138062-(2-(5-fluoropyridin-2-yl)-1,3-dioxolan-2-yl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone from Example 1 and toluene are added ethylene glycol 5 equiv) and p-toluenesulfonic acid monohydrate (0.2 equiv), and the mixture is heated at reflux while collecting water in a Dean-Stark trap. As needed, additional ethylene glycol and p-toluenesulfonic acid monohydrate are added and heating and water collection are continued to achieve substantially complete reaction After cooling to rt, the mixture is concentrated, and the residue is dissolved in DMSO and purified by reverse phase HPLC.

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. customwhile collecting water in a Dean-Stark trap
  4. additionadditional ethylene glycol and p-toluenesulfonic acid monohydrate are added
  5. temperatureheating
  6. customwater collection
  7. customreaction
  8. concentrationthe mixture is concentrated
  9. dissolutionthe residue is dissolved in DMSO
  10. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-492ba060af3e410faad8723626d80941
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633207B2

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