Potassium Carbonate → HCID 21842452, compound

HRID 1737240Notes

Reaction equation

HRID 1737240 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[Cl:17])[N:7]=[C:6]([N:18]2[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19]2)[N:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1>[ClH:16].[NH2:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[Cl:17])[N:7]=[C:6]([N:18]2[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:19]2)[N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 21842411HCID 21842411, compound

Product 1

HCID 21842452HCID 21842452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 40 ml of THF was dissolved 2.1 g of the free base obtained by neutralizing the compound of Example 62, followed by addition of 0.94 g of potassium carbonate and 0.78 g of methanesulfonyl chloride. The mixture was reacted at room temperature for 20 hours. The THF was removed by concentration and the residue was diluted with water and extracted with chloroform. The extract was washed with water and dried and the chloroform was distilled off. The residue was purified by silica gel column chromatography (elution with CHCl3 :MeOH=19:1) and the resulting oil, 2.3 g, was treated in the same manner as in Example 32 (Step 2) to provide the title compound. m.p. 220-230° C.

Workup

  1. customobtained
  2. customThe mixture was reacted at room temperature for 20 hours
  3. customThe THF was removed by concentration
  4. additionthe residue was diluted with water
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. customdried
  8. distillationthe chloroform was distilled off
  9. customThe residue was purified by silica gel column chromatography (elution with CHCl3 :MeOH=19:1)
  10. additionthe resulting oil, 2.3 g, was treated in the same manner as in Example 32 (Step 2)

Sources & evidence

ORD record
ord-2fba83cf48c64044bff02078ca9c4e09
Source dataset
uspto-grants-1999_10
Patent number
US05962453

Reaction notes

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