Sodium Iodide → HCID 68917663, compound

HRID 1929744Notes

Reaction equation

HRID 1929744 reaction equation
[NH2:1][C:2]1[C:24]([C:25](=[O:32])[NH:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:5]2[N:6]=[CH:7][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.Cl[CH2:34][CH2:35][CH2:36][CH2:37]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(#N)C.O.C(OCC)(=O)C>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:8]1[CH:7]=[N:6][C:5]2[N:4]([N:3]=[C:2]([N:1]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[C:24]=2[C:25](=[O:32])[NH:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:9]=1[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 80591,4-DichlorobutaneHCID 11430Potassium CarbonateHCID 67272527HCID 67272527, compound

Product 1

HCID 68917663HCID 68917663, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

To a solution of the compound obtained in Example 40 (60 mg) in water/acetonitrile (0.3 mL/2.4 mL) was added 1,4-dichlorobutane (81.6 mg), potassium carbonate (88.8 mg) and sodium iodide (6.8 mg) and the mixture was stirred at 150° C. for 3 hours in a microwave reactor. After cooling to room temperature, to the reaction mixture was added ethyl acetate and water and the mixture was stirred. The organic layer was extracted and dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=90/10 to 70/30) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)-2-(1-pyrrolidinyl)-pyrazolo[1,5-a]pyrimidine (25 mg; yield: 37%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. stirringthe mixture was stirred
  3. extractionThe organic layer was extracted
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=90/10 to 70/30)

Sources & evidence

ORD record
ord-c7ba9b4941ff487ca677c8236753e67e
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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