1-Bromo-3-chloropropane → 5-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole

HRID 429374노트

반응식

HRID 429374 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1.Br[CH2:24][CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:24][CH2:25][CH2:26][Cl:27])[CH:16]=1

참가 물질

6

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 222628105-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole

생성물 1

HCID 222628035-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole수율 33.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

5-amino-4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole (0.5 g, 1.6 mmol), 1-bromo-3-chloropropane (0.26 g, 1.6 mmol) and cesium carbonate (0.52 g, 1.6 mmol) in dimethylformamide (25 ml) was heated at 80° C. After 2 days, the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes) to give 5-amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole (0.2 g) as a solid.

후처리

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes)

출처 및 근거

ORD 기록
ord-9566262071704cd5bb3bf67d3d3ebe85
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316466B1

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