1,1'-Carbonyldiimidazole → 3-Benzyloxy-1-(2,4-difluorophenyl)-6,7-difluoro-1H-quinazoline-2,4-dione

HRID 2270254노트

반응식

HRID 2270254 반응식
[CH2:1]([O:8][NH:9][C:10](=[O:28])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30]>C1COCC1>[CH2:1]([O:8][N:9]1[C:10](=[O:28])[C:11]2[C:12](=[CH:13][C:14]([F:18])=[C:15]([F:17])[CH:16]=2)[N:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C:29]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22632987N-Benzyloxy-2-(2,4-difluoroanilino)-4,5-difluoro-benzamide

생성물 1

HCID 226329863-Benzyloxy-1-(2,4-difluorophenyl)-6,7-difluoro-1H-quinazoline-2,4-dione수율 68.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-benzyloxy-2-(2,4-difluoroanilino)-4,5-difluoro-benzamide (Example I-4, 5.66 g, 15 mmol) and carbonyldiimidazole (2.83 g, 17 mmol) were combined in 300 mL of THF and heated to reflux for 30 hours. The solution was cooled, concentrated, and redissolved in chloroform. The solution was washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 4.25 g of a solid which was purified by column chromatography (silica gel, CHCl3/MeOH, 98:2) to give 2.0 g of the title compound as a solid.

후처리

  1. temperatureheated
  2. temperatureto reflux for 30 hours
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. dissolutionredissolved in chloroform
  6. washThe solution was washed with 1N HCl, saturated NaHCO3, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

출처 및 근거

ORD 기록
ord-0297fa37487740ae9ce2aef095fc373f
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06331538B1

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