Sodium Iodide → HCID 15549658, compound

HRID 1250308Notes

Reaction equation

HRID 1250308 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]=[CH:9][N:8]([CH2:12][CH2:13]Cl)[C:7](=[O:15])[C:6]=2[CH:16]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[I-].[Na+].C(N(CC)CC)C.C([O-])(=O)/C=C/C([O-])=O>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]=[CH:9][N:8]([CH2:12][CH2:13][N:26]3[CH2:27][CH2:28][N:23]([C:18]4[N:17]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH2:24][CH2:25]3)[C:7](=[O:15])[C:6]=2[CH:16]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 5460307FumarateHCID 15542506HCID 15542506, compound

Product 1

HCID 15549658HCID 15549658, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

14 mg of the compound of Example 1 was dissolved in 5 ml of dimethylformamide, 13 mg (1.5 equivalents) of 1-(2-pyrimidinyl)piperazine, 16 mg (2 equivalents) of sodium iodide, and 11 mg (2 equivalents) of triethylamine. were added, and the resultant mixture was agitated at 90° C. for 10 hours. This was allowed to cool, then water was added and extraction was performed twice with ethyl acetate. The entire organic layer was washed with an aqueous solution of sodium hydrogencarbonate, water, and saturated saline, then was dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant crude product was refined with silica gel column chromatography (methylene chloride:methanol=30:1) to obtain the above-referenced compound in an amount of 14 mg (yield of 67%). Note that the fumarate can be obtained by an ordinary method, then making it into an amorphous powder.

Workup

  1. additionwere added
  2. temperatureto cool
  3. extractionextraction
  4. washThe entire organic layer was washed with an aqueous solution of sodium hydrogencarbonate, water, and saturated saline
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain the above-referenced compound in an amount of 14 mg (yield of 67%)
  8. customcan be obtained by an ordinary method

Sources & evidence

ORD record
ord-b7802e3cef0f4f7caa1d12ab3a0d8d73
Source dataset
uspto-grants-2002_01
Patent number
US06337397B1

Reaction notes

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