2-Propanol, sodium salt (1:1) → 6-Ethoxy-8-isopropoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 1524489Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:14][CH2:15][CH3:16])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1)[CH3:2].[CH3:17]C(C)[O-].[Na+]>C(O)(C)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:14][CH:15]([CH3:17])[CH3:16])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1)[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

6,8-Diethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W1.126; 80 mg, 0.358 mmol) was dissolved in isopropanol (10 ml), and sodium isopropoxide (297 mg) was added. The mixture was heated to 85° C. for 1 h and concentrated, the residue was dissolved in water and a pH of 6 was established by adding aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined organic phases were dried and concentrated. The remaining residue was purified by flash chromatography (dichloromethane:MeOH). Yield: 58 mg.

Workup

concentrationconcentrated
dissolutionthe residue was dissolved in water
additionby adding aqueous hydrochloric acid
extractionThe mixture was extracted with ethyl acetate
customthe combined organic phases were dried
concentrationconcentrated
customThe remaining residue was purified by flash chromatography (dichloromethane:MeOH)

Sources & evidence

ORD record: ord-aee8bbcaf5ed4a19b5f5662eaa803aef
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079906B2

Reaction notes

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