Water → 8-Methyl-6-[2-(tetrahydropyran-2-yloxy)ethoxy]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657862

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][OH:10].[H-].[Na+].Br.Cl[C:15]1[CH:16]=[C:17]([CH3:25])[C:18]2[N:19]([C:21]([NH2:24])=[N:22][N:23]=2)[N:20]=1.O>CN(C=O)C>[CH3:25][C:17]1[C:18]2[N:19]([C:21]([NH2:24])=[N:22][N:23]=2)[N:20]=[C:15]([O:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2-(Tetrahydropyran-2-yloxy)ethanol (3.85 ml) was initially charged in DMF (25 ml), admixed under argon with sodium hydride (681 mg) and stirred at 40° C. for 0.5 h. Subsequently, 6-chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 1.5 g), dissolved in DMF (25 ml), was added dropwise. After 40 min, the mixture was admixed with water and extracted by shaking four times with dichloromethane. To eliminate the excess alcohol, the mixture was chromatographed first through a short silica gel column with MtB ether and then with 8:2 dichloromethane/methanol. The clean product fractions were combined and dried. 678 mg of the title compound were obtained.

Workup

additionwas added dropwise
waitAfter 40 min
extractionextracted
stirringby shaking four times with dichloromethane
customthe mixture was chromatographed first through a short silica gel column with MtB ether
customdried

Sources & evidence

ORD record: ord-53e71004c55345a8923e3d45c877db14
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Linked notes

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