Dimethyl Sulfoxide → HCID 9798400, compound

HRID 1939924Notes

Reaction equation

HRID 1939924 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH2:21][CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:16][CH:15]=2)=[O:8])[CH:2]=1.Br.C(O)(=O)C.CS(C)=O.C(OC(C)C)(C)C>C(O)(=O)C.C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:16][CH:15]=2)=[O:8])[CH:2]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7914Diisopropyl EtherHCID 18977189HCID 18977189, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 9798400HCID 9798400, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In acetic acid (100 ml) was dissolved 10.0 g of 6-[4-(4-(pyridin-3-ylcarbonylamino)butyl)phenyl]-4,5-dihydropyridazin-3(2H)-one. 25 % hydrogen bromide-acetic acid (100 ml) was added to the solution, and the mixture was stirred at room temperature for 5 minutes. 2.9 g of dimethylsulfoxide was added to the mixture at room temperature, and the resulting mixture was stirred at the same temperature for 1 hour. Ethanol (150 ml) was added to the reaction mixture, and the mixture was stirred for 2 hours. Diisopropyl ether (150 ml) was further added to the mixture, and the resulting mixture was stirred for 2 hours. Precipitated crystal was collected by filtration, washed with diisopropyl ether and then dissolved in hydrated ethanol, and the solution was neutralized with aqueous ammonia. Precipitated crystal was collected by filtration, washed with water and then recrystallized from methanol to obtain 8.9 g of 6-[4-(4-(pyridin-3-ylcarbonylamino)butyl)phenyl]pyridazin-3(2H)-one.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  2. stirringthe mixture was stirred for 2 hours
  3. stirringthe resulting mixture was stirred for 2 hours
  4. customPrecipitated crystal
  5. filtrationwas collected by filtration
  6. washwashed with diisopropyl ether
  7. dissolutiondissolved in hydrated ethanol
  8. customPrecipitated crystal
  9. filtrationwas collected by filtration
  10. washwashed with water
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f136f0bb397f4aee84d2f168eb94704f
Source dataset
uspto-grants-1997_12
Patent number
US05698554

Reaction notes

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