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Ethylene Glycol → 4-(6-Pyridin-2-yl-2,3-dihydro-pyrazolo[5,1-b]oxazol-7-yl)-quinoline

HRID 8280
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HRID 8280 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[C:9]([OH:12])[NH:10][N:11]=1.[CH2:23](O)[CH2:24]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[C:9]2[O:12][CH2:23][CH2:24][N:10]2[N:11]=1
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참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 178418827HCID 178418827, 화합물

생성물 1

HCID 99228524-(6-Pyridin-2-yl-2,3-dihydro-pyrazolo[5,1-b]oxazol-7-yl)-quinoline수율 74.9%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 5-pyridin-2-yl-4-quinolin-4-yl 2H-pyrazol-3-ol (50 mg, 0.17 mmol), ethylene glycol (15 mg, 0.24 mmol) and tri-n-butylphosphine (100 mg, 0.50 mmol) in tetrahydrofuran (15 mL) is added 1,1′-(azodicarbonyl)dipiperidine (120 mg, 0.48 mmol). The solution is heated at reflux for 5 h, cooled, and filtered through an SCX cartridge. The residue is chromatographed on SiO2 (15:1 dichloromethane:methanol). The product residue is converted to the disoxylate salt to give the title compound 40 mg (46%).

후처리

  1. temperatureThe solution is heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled
  4. filtrationfiltered through an SCX cartridge
  5. customThe residue is chromatographed on SiO2 (15:1 dichloromethane:methanol)

출처 및 근거

ORD 기록
ord-4764fcefb6504a36872261252b2115e7
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087626B2

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