Water → HCID 58136921, compound

HRID 217679Notes

Reaction equation

HRID 217679 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]([CH2:15][CH3:16])=[C:6]([CH3:14])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1.[OH2:17].ClCCl>CCC(O)CC.CN(C=O)C>[CH2:15]([C:5]1[C:4]([O:17][CH:5]([CH2:15][CH3:16])[CH2:6][CH3:7])=[N:9][N:8]2[C:10]([NH2:13])=[N:11][N:12]=[C:7]2[C:6]=1[CH3:14])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 58136934HCID 58136934, compound

Product 1

HCID 58136921HCID 58136921, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 114283-PentanolSolvent2×

Procedure

3-Pentanol (2.5 ml) was initially charged at RT with stirring. Thereafter, sodium hydride (91 mg) was added while cooling with ice. After stirring at 55° C. for 2.5 h, 6-chloro-7-ethyl-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.007; 120 mg), dissolved in 3-pentanol (2 ml) and DMF (4 ml), was added dropwise. After stirring for 1 h, the mixture was left to stand at RT overnight, and the reaction mixture was admixed with water and dichloromethane and then 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. 126 mg of the title compound were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringAfter stirring at 55° C. for 2.5 h
  3. stirringAfter stirring for 1 h
  4. waitthe mixture was left
  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-5193005dc181472489104a3a95f3b1c1
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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