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

HRID 2036084
Notes
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Reaction equation

HRID 2036084 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:19][CH2:18][C:17]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH2:20]2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:19][CH2:18][C:17]4([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[O:21][CH2:20]4)[CH2:16][CH2:15]3)=[CH:7][CH:6]=2)[S:12][N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 109218293-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazineHCID 151870462H-Spiro(1-benzofuran-3,4'-piperidine)

Product 1

HCID 250006571'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]spiro[1-benzofuran-3,4'-piperidine]Yield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution (4 ml) of 3-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazine (69 mg), spiro[1-benzofuran-3,4′-piperidine] (62 mg) and potassium carbonate (54 mg) in N,N-dimethylformamide was stirred at 70° 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 purified by silica gel chromatography (33% ethyl acetate/hexane) to give the object product (42 mg, 35%).

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. customThe residue was purified by silica gel chromatography (33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f7bb8bc700d842668f9c51a7bd3eb42b
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575167B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes