Water → 6-(2-Methoxy-1-methoxymethylethoxy)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657860

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]([OH:8])[CH2:5][O:6][CH3:7].[H-].[Na+].Br.Cl[C:13]1[CH:14]=[C:15]([CH3:23])[C:16]2[N:17]([C:19]([NH2:22])=[N:20][N:21]=2)[N:18]=1.O>CN(C=O)C>[CH3:1][O:2][CH2:3][CH:4]([CH2:5][O:6][CH3:7])[O:8][C:13]1[CH:14]=[C:15]([CH3:23])[C:16]2[N:17]([C:19]([NH2:22])=[N:20][N:21]=2)[N:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

1,3-Dimethoxypropan-2-ol (12.96 ml) was initially charged in DMF (25 ml), admixed under argon with sodium hydride (681 mg) and stirred at 40° C. for 1 h. Subsequently, 6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 1.5 g), dissolved in DMF (25 ml), was added dropwise within 20 min. After 1 h, the mixture was admixed with water and extracted by shaking four times with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated by rotary evaporation. The residue was triturated with MtB ether, filtered off with suction and dried. 764 mg of the title compound were isolated. LC-MS rt: 0.74 min [M+H]+: 268.1 (met. a)

Workup

additionwas added dropwise within 20 min
waitAfter 1 h
extractionextracted
stirringby shaking four times with dichloromethane
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated by rotary evaporation
customThe residue was triturated with MtB ether
filtrationfiltered off with suction
customdried

Sources & evidence

ORD record: ord-fbede180588444a09ed2d48ec861c335
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Linked notes

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