Water → HCID 66935818, compound

HRID 217687Notes

Reaction equation

HRID 217687 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]([CH3:16])=[C:6]([CH3:15])[C:7]2[N:8]([C:10]([CH2:13][NH2:14])=[N:11][N:12]=2)[N:9]=1.O.ClCCl.[CH3:21][CH2:22][CH:23]([OH:26])[CH2:24][CH3:25]>CN(C=O)C>[CH2:22]([CH:23]([O:26][C:4]1[C:5]([CH3:16])=[C:6]([CH3:15])[C:7]2[N:8]([C:10]([CH2:13][NH2:14])=[N:11][N:12]=2)[N:9]=1)[CH2:24][CH3:25])[CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 114283-Pentanol2×HCID 24758Sodium hydrideHCID 86650802HCID 86650802, compound

Product 1

HCID 66935818HCID 66935818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 3 h, (6-chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylamine (W2.169; 50 mg), dissolved in 3-pentanol (1 ml) and DMF (2 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 magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 44 mg of the title compound were obtained. LC-MS rt: 0.86 min [M+H]+: 264.2 (met. b)

Workup

  1. temperaturewhile cooling with ice
  2. stirringAfter stirring at 55° C. for 3 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 magnesium sulfate
  7. filtrationafter the desiccant had been filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-de56b59ef54b422582f5dde621091aa1
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

Loading…