Diethyl Oxalate → 5-(4-Fluorobenzyl)-7,8-dihydroxy-5H-pyrido[1,2-a]quinoxaline-6,10-dione

HRID 2109868노트

반응식

HRID 2109868 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:6](=[O:22])[CH2:5]1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[C:38](OCC)(=[O:44])[C:39](OCC)=[O:40]>CN(C=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:4]3[C:1](=[O:3])[CH:2]=[C:38]([OH:44])[C:39]([OH:40])=[C:5]3[C:6]2=[O:22])=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 7268Diethyl OxalateHCID 8028Tetrahydrofuran2회HCID 2733832Lithium Hexamethyldisilazide2회HCID 576346374-Acetyl-1-(4-fluorobenzyl)-3,4-dihydroquinoxalin-2(1H)-one

생성물 1

HCID 546763045-(4-Fluorobenzyl)-7,8-dihydroxy-5H-pyrido[1,2-a]quinoxaline-6,10-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a cold (0° C.) solution of 4-acetyl-1-(4-fluorobenzyl)-3,4-dihydro-quinoxalin-2(1H)-one (0.15 g, 0.52 mmol) in DMF (5 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)amide in THF (0.57 mL, 0.57 mmol) was added and stirred at the temperature for 30 min. The resultant solution was treated with diethyl oxalate (0.078 mL, 0.57 mmol), and stirred at room temperature overnight. The resultant mixture was then treated with additional lithium bis(trimethylsilyl)amide in THF (1.6 mL, 1.6 mmol) and stirred at room temperature for 6 h. The product mixture was concentrated under vacuum, and the residue partitioned between aqueous HCl and dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as white solid.

후처리

  1. stirringstirred at room temperature overnight
  2. stirringstirred at room temperature for 6 h
  3. concentrationThe product mixture was concentrated under vacuum
  4. customthe residue partitioned between aqueous HCl and dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was subjected to HPLC purification on C-18 stationary phase
  10. washeluted with water/acetonitrile/TFA mobile phase
  11. customCollection and lyophilization of appropriate fractions

출처 및 근거

ORD 기록
ord-395b3531427444dc9893bc12e1457854
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517532B2

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