Potassium Iodide → HCID 44479892, compound

HRID 1647810Notes

Reaction equation

HRID 1647810 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][CH2:18]CS([O-])(=O)=O)(=[O:4])=[O:3].[I-].[K+].C(N(CC)C(C)C)(C)C.[CH3:35][O:36][C:37]1[C:38]([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[N:39][CH:40]=[N:41][CH:42]=1>C(#N)C.C(Cl)Cl>[CH3:35][O:36][C:37]1[C:38]([N:43]2[CH2:48][CH2:47][N:46]([CH2:18][CH2:17][CH2:16][C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:8]=4)[NH:12][CH:11]=3)[CH2:45][CH2:44]2)=[N:39][CH:40]=[N:41][CH:42]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 104201525-Methoxy-4-(piperazin-1-yl)pyrimidineHCID 199216343-[5-[[(methylsulfonyl)amino]methyl]-1H-indol-3-yl]propylmethanesulfonate

Product 1

HCID 44479892HCID 44479892, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 3-[5-[[(methylsulfonyl)amino]methyl]-1H-indol-3-yl]propylmethanesulfonate (15.1 mmol, 1.0 equiv.) in 200 mL of anhydrous acetonitrile were added 2.51 g (15.1 mmol, 1.0 equiv.) of potassium iodide, 3.15 mL of N,N-diisopropylethylamine and 3.23 g of 1-(5-methoxy-4-pyrimidinyl)piperazine. The mixture was heated to reflux for 48 hours. The reaction mixture was cooled to room temperature, filtered and concentrated. The residue was dissolved in 250 mL of chloroform, washed with 50 mL portions of 10% aqueous potassium carbonate and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield an oil. Chromatography on silica gel using 7.5% methanol in methylene chloride containing 0.75% concentrated aqueous ammonium hydroxide gave 3.93 g (57%) of 4-(5-methoxy-4-pyrimidinyl)-1-[[5-[[(methylsulfonyl)amino]methyl]-1H-indol-3-yl]propyl]piperazine. The hydrochloride was prepared by addition of 3N ethanolic HCl to an ethanolic solution of the base. Recrystallization from ethanol followed by drying in vacuo at 65° C. gave 0.268 g (53%) of the hydrochloride ethanolate: C22H30N6O3S/2.4 HCl/0.4 C2H6O, m.p. 204°-206° C. Elemental analysis calculated C, 48.51; H, 6.21; N, 14.89; found: C, 48.59; H, 6.21; N, 14.95.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 250 mL of chloroform
  6. washwashed with 50 mL portions of 10% aqueous potassium carbonate and saturated aqueous sodium chloride
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield an oil

Sources & evidence

ORD record
ord-0c4b53a6d64e4f4d808cd2dded4821d0
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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