Water → HCID 58045991, compound

HRID 657889Notes

Reaction equation

HRID 657889 reaction equation
[H-].[Na+].Cl[C:4]1[CH:5]=[C:6]([CH2:14][CH3:15])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1.[OH2:16].ClCCl>CCC(O)CC.CN(C=O)C>[CH2:14]([C:6]1[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=[C:4]([O:16][CH:6]([CH2:14][CH3:15])[CH2:5][CH3:4])[CH:5]=1)[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 58045769HCID 58045769, compound

Product 1

HCID 58045991HCID 58045991, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 114283-PentanolSolvent2×

Procedure

3-Pentanol (1.2 ml) was initially charged at RT with stirring. Thereafter, sodium hydride (77 mg) was added while cooling with ice. After stirring at 55° C. for 2.5 h, 6-chloro-8-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.003, 60 mg), dissolved in 3-pentanol (1.5 ml) and 4 ml of DMF (4 ml), was added dropwise. After stirring for 2 h, the reaction mixture was left to stand at RT overnight, admixed with water and dichloromethane and then extracted three times more with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 70 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 2 h
  4. waitthe reaction mixture was left
  5. extractionextracted three times more 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-8ef8796052e74ee689864247cd32404c
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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