Potassium Carbonate → 1'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one

HRID 2036118노트

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HRID 2036118 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:18][CH2:17][C:16]2([C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])[CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:15]3)=[CH:7][CH:6]=2)[O:12][N:11]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 10954296Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-oneHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine

생성물 1

HCID 685546001'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one수율 62%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 8857Ethyl Acetate용매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

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온도
120 °C

실험 절차

3-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (690 mg) obtained in Example 43(2), spiro[indole-3,3′-pyrrolidin]-2(1H)-one (800 mg), potassium carbonate (500 mg) and tetrabutylammonium iodide (130 mg) were suspended in N,N-dimethylformamide-tetrahydrofuran (1:1, v/v, 50 mL), and the suspension was stirred at 120° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with aqueous sodium carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. Ethyl acetate was added and the resulting precipitate was collected by filtration, and recrystallized from ethyl acetate to give the object product (750 mg, 62%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with aqueous sodium carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate was added
  6. filtrationthe resulting precipitate was collected by filtration
  7. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-8b967e958ac5430e88063481c8156955
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575167B2

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