Diethyl Oxalate → 6,7-Difluoroquinoxaline-2,3(1H,4H)-dione

HRID 1068589ノート

反応式

HRID 1068589 の反応式
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([NH2:19])=[C:14]([NH2:20])[CH:13]=1>>[F:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][C:17]=1[F:18])[NH:19][C:1](=[O:8])[C:2](=[O:4])[NH:20]2

参加物

3

反応物 2

HCID 7268Diethyl OxalateHCID 27367551,2-Diamino-4,5-difluorobenzene

生成物 1

HCID 8228396,7-Difluoroquinoxaline-2,3(1H,4H)-dione

実験手順

The title compound (Sarges, R. et al., J. Med. Chem. 33.2240 (1990)) was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Cam. Soc. 1171 (1962)). A mixture of diethyl oxalate (1.11 g, 7.63 mmol and 4,5-difluoro-1,2-diaminobenzene (110 mg, 0.763 mmol) was heated to reflux under N2 for 2 h. The reaction was allowed to cool to room temperature and the solid was collected by vacuum filtration, rinsed with hexanes, and air dried. This gray brown solid was recrystallized from 20 mL of EtOH and the brown-white crystals collected by vacuum filtration and the crystals further dried under vacuum (0.5 torr, 25° C.) to yield 45.3 mg (30.0%); mp >360° C. (lit. >310° C.); 1H NMR (d6-acetone) δ 7.19 (t, 2H, ArH, JH-F=9.3), 10.9 (br s, 2H, NH).

後処理

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 2 h
  3. filtrationthe solid was collected by vacuum filtration
  4. washrinsed with hexanes, and air
  5. customdried
  6. customThis gray brown solid was recrystallized from 20 mL of EtOH
  7. filtrationthe brown-white crystals collected by vacuum filtration
  8. customthe crystals further dried under vacuum (0.5 torr, 25° C.)
  9. customto yield 45.3 mg (30.0%)
  10. custommp >360° C. (lit. >310° C.)

出典と根拠

ORDレコード
ord-f3301b631ce841988542bc08c9a97de0
出典データセット
uspto-grants-2001_06
特許番号
US06251903B1

反応ノート

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