Water → HCID 58136921, compound

HRID 657878Notes

Reaction equation

HRID 657878 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-915640ae990245518b5b9e2424a336a6
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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