Sodium Iodide → HCID 15293733, compound

HRID 1648492Notes

Reaction equation

HRID 1648492 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([NH2:13])=[O:12])[NH:6]2.[N:14]1([C:20]2[CH:25]=[C:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[N:23]=[C:22]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:21]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:36](=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:44](#N)[CH3:45]>>[N:31]1([C:22]2[N:23]=[C:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:25]=[C:20]([N:14]3[CH2:19][CH2:18][N:17]([CH2:36][CH2:44][CH2:45][O:1][C:2]4[CH:10]=[CH:9][CH:8]=[C:7]5[C:3]=4[CH:4]=[C:5]([C:11]([NH2:13])=[O:12])[NH:6]5)[CH2:16][CH2:15]3)[N:21]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 15054039HCID 15054039, compound

Product 1

HCID 15293733HCID 15293733, compound

Procedure

The 4-hydroxyindole-2-carboxamide (EXAMPLE 5, 0.44 g), 4-(1-piperazinyl)-2,6-di-1-pyrrolidinylpyrimidine (0.525 g, 1.74 mmol), powdered potassium carbonate (0.12 g, 0.87 mmol) and sodium iodide (0.075 g) are combined in acetonitrile (50 ml) and heated at reflux for 96 hr. Although TLC showed starting material remained in the reaction mixture, the mixture is 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 4-[3-[4-[2,4-dipyrrolidino-6pyrimidinyl]-1-piperazinyl]propoxy]indole-2-carboxamide, 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 is 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-bc5f4661f6444d068f88b0183c2adae7
Source dataset
uspto-grants-1995_07
Patent number
US05436337

Reaction notes

Loading…