3-Pentanol → HCID 58045750, compound

HRID 657890Notes

Reaction equation

HRID 657890 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]([CH3:14])=[CH:6][C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1.[CH3:15][CH2:16][CH:17]([OH:20])[CH2:18][CH3:19]>CN(C=O)C>[CH2:16]([CH:17]([O:20][C:4]1[C:5]([CH3:14])=[CH:6][C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1)[CH2:18][CH3:19])[CH3:15]

Participants

5

Reactant 3

HCID 114283-Pentanol2×HCID 24758Sodium hydrideHCID 58045884HCID 58045884, compound

Product 1

HCID 58045750HCID 58045750, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-Pentanol (30 ml) was initially charged under argon, admixed with sodium hydride (1.48 g) and stirred at 50° C. for 1 h. Subsequently, 6-chloro-7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.005, 1.88 g), dissolved in 3-pentanol (130 ml) and DMF (60 ml), was slowly added dropwise within 1 h. After stirring for 1 h, the mixture was concentrated, and the residue was admixed with water and extracted four times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using an 80 g silica gel cartridge (0-10% dichloromethane-methanol gradient in 40 min). The clean product fractions were combined and dried. 1.25 g of the title compound were obtained.

Workup

  1. stirringAfter stirring for 1 h
  2. concentrationthe mixture was concentrated
  3. extractionextracted four times with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customan 80 g silica gel cartridge (0-10% dichloromethane-methanol gradient in 40 min)
  9. customdried

Sources & evidence

ORD record
ord-038ffd245d744673975c5d9990a36ccb
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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