4-Hydrazinobenzoic acid → 4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

HRID 1817056노트

반응식

HRID 1817056 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([C:12]([O-:14])=O)=[C:7]2O.[NH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[NH2:17]>S(Cl)(Cl)=O.C(O)C>[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:14])[N:16]([C:18]4[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:25][CH:26]=4)[NH:17][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 120894-Hydrazinobenzoic acidHCID 178524933HCID 178524933, 화합물

생성물 1

HCID 589748824-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 24386Thionyl Chloride용매

실험 절차

Crude 8-Fluoro-4-hydroxycinnoline-3-carboxylate from the previous stage (1.00 g, 4.95 mmol) was dissolved in thionyl chloride (50 ml). The solution was heated to reflux for 2-3 h until no further gas evolution was observed. The reaction mixture was cooled to room temperature and excess thionyl chloride was removed under vacuum. The crude intermediate was azeotroped with toluene (3×25 ml). A dark brown solid was obtained, which was taken up in ethanol (25 ml). 4-Hydrazinobenzoic acid (640 mg, 4.21 mmol) was added and the mixture was stirred at room temperature overnight. The solids were collected by filtration, slurried in 1 M HCl (100 ml), filtered, washed with hexane (50 ml) and dried under vacuum. A brown solid was obtained (890 mg of crude product). LCMS: m/z [M+H]+ 325.

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2-3 h until no further gas evolution
  3. customexcess thionyl chloride was removed under vacuum
  4. customThe crude intermediate was azeotroped with toluene (3×25 ml)
  5. customA dark brown solid was obtained
  6. filtrationThe solids were collected by filtration
  7. filtrationfiltered
  8. washwashed with hexane (50 ml)
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-e3ecf307be0f46c29b8d605907d35510
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598247B2

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