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

HRID 2036125Notes

Reaction equation

HRID 2036125 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.Cl.[NH:15]1[CH2:19][CH2:18][C:17]2([CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20]2)[CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:15]3[CH2:19][CH2:18][C:17]4([CH2:23][C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[O:20]4)[CH2:16]3)=[CH:7][CH:6]=2)[O:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazineHCID 203942743H-spiro[1-benzofuran-2,3'-pyrrolidine] hydrochloride

Product 1

HCID 250010011'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]-3H-spiro[1-benzofuran-2,3'-pyrrolidine]Yield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (39 mg) obtained in Example 43(2), 3H-spiro[1-benzofuran-2,3′-pyrrolidine] hydrochloride (42 mg) and potassium carbonate (55 mg) was stirred in DMF (5 mL) at 120° C. overnight. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was washed with a small amount of acetic acid to give the object product (35 mg, 52%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated
  6. washThe residue was washed with a small amount of acetic acid

Sources & evidence

ORD record
ord-8cb62c7e6e9f482ea69a2e0fbd60d8e2
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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