Water → HCID 135474306, compound

HRID 1783311Notes

Reaction equation

HRID 1783311 reaction equation
Br[CH2:2][C:3]1[C:15]2[C:14]3[CH:13]=[CH:12][C:11]([F:16])=[CH:10][C:9]=3[C:8]([O:17]COC)=[N:7][C:6]=2[N:5]([CH3:21])[N:4]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24]C1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:16][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:3]([CH2:2][N:22]4[CH2:24][CH2:25][CH2:26][CH2:27]4)=[N:4][N:5]([CH3:21])[C:6]=3[NH:7][C:8](=[O:17])[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 23084607HCID 23084607, compound

Product 1

HCID 135474306HCID 135474306, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After the completion of the reaction, the reaction solution was allowed to cool to room temperature, and the precipitated solid was removed by filtration. The filtrate was concentrated, and the residue was filtrated using silica gel (hexane:ethyl acetate=2:1). The filtrate was concentrated to give 1-bromomethyl-7-fluoro-5-methoxymethoxy-3-methyl-3H-pyrazolo[3,4-c]isoquinoline (0.50 g) as crude crystals. The crude crystals (0.50 g) of 1-bromomethyl-7-fluoro-5-methoxymethoxy-3-methyl-3H-pyrazolo[3,4-c]isoquinoline, piperidine (0.30 g) and potassium carbonate (0.39 g) were dissolved in acetonitrile (20 mL), and the reaction solution was stirred at room temperature for 2 days. After the completion of the reaction, the reaction solution was poured into water and extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give 7-fluoro-3-methyl-1-(pyrrolidin-1-ylmethyl)-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one (0.079 g).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-b3ca704589bc463f87fa7c77d7e5fcbd
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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