Water → HCID 58046037, compound

HRID 657882Notes

Reaction equation

HRID 657882 reaction equation
Cl[C:2]1[C:3]([CH2:14][CH3:15])=[C:4]([CH2:12][CH3:13])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.[O-:16][CH2:17][CH3:18].[Na+].O>C(O)C>[CH2:17]([O:16][C:2]1[C:3]([CH2:14][CH3:15])=[C:4]([CH2:12][CH3:13])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1)[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxide3×HCID 58045795HCID 58045795, compound

Product 1

HCID 58046037HCID 58046037, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-7,8-diethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.014, 0.1 g) was dissolved in ethanol (13 ml) while stirring and under argon. Thereafter, the reaction mixture was admixed with sodium ethoxide (61 mg) and stirred at RT for 1 h, then at 55° C. for 30 min. Subsequently, a further 2 equivalents of sodium ethoxide were added and the mixture was stirred at 55° C. for 4.5 h. After another 1 equivalent of sodium ethoxide had been added, the mixture was stirred at 55° C. for 2.5 h and left to stand over the weekend. The solvent was then drawn off, and the residue was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 92 mg of the title compound were obtained. LC-MS rt: 0.80 min [M+H]+: 236.2 (met. b)

Workup

  1. stirringstirred at RT for 1 h
  2. stirringthe mixture was stirred at 55° C. for 4.5 h
  3. stirringthe mixture was stirred at 55° C. for 2.5 h
  4. waitleft
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationafter the desiccant had been filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2d0dc0b71c1d415289f1f1329d1d4627
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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