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

HRID 2036118Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-8b967e958ac5430e88063481c8156955
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575167B2

Reaction notes

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