N-methyl-2-pyrrolidone → 3-Benzoyl-7-chloropyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

HRID 428432노트

반응식

HRID 428432 반응식
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:9]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:10][NH:11][C:12]=2[C:13]([O:15]CC)=O)=[O:7])=[C:4]([NH2:28])[CH:3]=1.CN1CCCC1=O.C([O-])(=O)C.[NH4+]>O>[C:18]([C:9]1[C:8]2[C:6](=[O:7])[C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][C:4]=3[NH:28][C:13](=[O:15])[C:12]=2[NH:11][N:10]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517165Ammonium AcetateHCID 18358872ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 183588743-Benzoyl-7-chloropyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione수율 5.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

A solution of ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate (620 mg, 1.56 mmol), 1-methyl-2-pyrrolidinone (4 mL) and ammonium acetate (120 mg, 1.56 mmol) was heated at 146° C. for 16.5 hours. The temperature was increased to 160° C. for 1 hour. The solution was allowed to cool to room temperature and water (60 mL) was added. The insoluble material (468 mg) was filtered, dried, and twice subjected to flash chromatography eluting with hexanes:ethyl acetate (90:10-50:50) to give impure product. The crude solid was triturated with ethanol (15 mL), washed with ethanol (3×10 mL) and dried to give the title compound (30.5 mg, 5.6% yield, m.p. 370-373° C. dec.).

후처리

  1. temperatureto cool to room temperature
  2. filtrationThe insoluble material (468 mg) was filtered
  3. customdried
  4. washeluting with hexanes:ethyl acetate (90:10-50:50)
  5. customto give impure product
  6. customThe crude solid was triturated with ethanol (15 mL)
  7. washwashed with ethanol (3×10 mL)
  8. customdried

출처 및 근거

ORD 기록
ord-766dad4bdd81449e807156f85a9550b9
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313290B1

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