Sodium Iodide → HCID 15293733, compound

HRID 1648490Notes

Reaction equation

HRID 1648490 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:15]([NH2:17])=[O:16])[NH:10]2.[N:18]1([C:24]2[CH:29]=[C:28]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:27]=[C:26]([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[N:35]1([C:26]2[N:27]=[C:28]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:29]=[C:24]([N:18]3[CH2:23][CH2:22][N:21]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[C:9]([C:15]([NH2:17])=[O:16])[NH:10]5)[CH2:20][CH2:19]3)[N:25]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 15293732HCID 15293732, compound

Product 1

HCID 15293733HCID 15293733, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(3-Chloropropoxy)indole-2-carboxamide (0.44 g), 4-(1-piperazinyl)-2,6-di-1-pyrrolidinylpyrimidine (0.525 g), powdered potassium carbonate (0.12 g) and sodium iodide (0.075 g) are combined in acetonitrile (50 ml) and heated at reflux for 96 hr. Although TLC showed both starting material and product remained in the reaction mixture, the mixture was concentrated under reduced pressure and the residue partitioned between 1N potassium bicarbonate and methylene chloride. The layers are separated, the aqueous layer is extracted with methylene chloride, the pooled organic extract is washed with water, then saline, dried over magnesium sulfate and concentrated. The residue is chromatographed over silica gel (250 ml) and eluted with methanol/methylene chloride (3.5/96.5). The appropriate fractions are pooled and concentrated. Crystallization from acetonitrile gives the title compound, mp 151°-2° (foam); the proposed structure is supported by NMR, IR and mass spectra.

Workup

  1. temperatureheated
  2. temperatureat reflux for 96 hr
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between 1N potassium bicarbonate and methylene chloride
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with methylene chloride
  7. extractionthe pooled organic extract
  8. washis washed with water
  9. dry with materialsaline, dried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue is chromatographed over silica gel (250 ml)
  12. washeluted with methanol/methylene chloride (3.5/96.5)
  13. concentrationconcentrated
  14. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-7b3322ffb51446ea9b3ad63852ba1155
Source dataset
uspto-grants-1995_07
Patent number
US05436337

Reaction notes

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