Water → 1'-[6-(3-Methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[1-benzofuran-3,3'-pyrrolidine]

HRID 2036110Notes

Reaction equation

HRID 2036110 reaction equation
[NH:1]1[CH2:5][CH2:4][C:3]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6]2)[CH2:2]1.Cl[C:15]1[N:16]=[N:17][C:18]([C:21]2[O:25][N:24]=[C:23]([CH3:26])[N:22]=2)=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:26][C:23]1[N:22]=[C:21]([C:18]2[N:17]=[N:16][C:15]([N:1]3[CH2:5][CH2:4][C:3]4([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[O:7][CH2:6]4)[CH2:2]3)=[CH:20][CH:19]=2)[O:25][N:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazineHCID 576662752H-spiro[benzofuran-3,3-pyrrolidine]

Product 1

HCID 250006581'-[6-(3-Methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[1-benzofuran-3,3'-pyrrolidine]Yield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution (5 ml) of spiro[1-benzofuran-3,3′-pyrrolidine] (50 mg) obtained in Example 50-(5) and 3-chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (56 mg) obtained in Example 43-(2) and potassium carbonate (79 mg) in N,N-dimethylformamide was stirred at 95° C. for 3 days. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was recrystallized from ethyl acetate to give the object product (45.1 mg, 47%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-552cfcb41a5c45528d8a41da278ea776
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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