Sodium Iodide → HCID 73863354, compound

HRID 1828245Notes

Reaction equation

HRID 1828245 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][C:9](=[N:11][OH:12])[C:8]2[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=2[S:6]1(=[O:18])=[O:17].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>C(#N)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][C:9](=[N:11][OH:12])[C:8]4[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=4[S:6]3(=[O:18])=[O:17])[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 752601-(4-Fluorophenyl)piperazineHCID 516892Sodium BicarbonateHCID 73863356HCID 73863356, compound

Product 1

HCID 73863354HCID 73863354, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 116 mg (0.4 mmol) of Compound 19, 108 mg (0.6 mmol) of 1-(4-fluorophenyl)piperazine, 134 mg (1.6 mmol) of sodium hydrogencarbonate and 120 mg (0.8 mmol) of sodium iodide in 8 ml of acetonitrile was refluxed for 23 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/20), whereby-152 mg of the title compound were obtained (yield: 87%).

Workup

  1. temperaturewas refluxed for 23 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/20)

Sources & evidence

ORD record
ord-f122f8cd55da42be82b666c871ebc41e
Source dataset
uspto-grants-2006_06
Patent number
US07057036B2

Reaction notes

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