Ethyl orthoformate → HCID 89619112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(6-aminopyridazin-3-yl)acetate (418 mg, 2.50 mmol) in acetic acid (10 mL) was added triethyl orthoformate (0.667 ml, 4.00 mmol), followed by sodium azide (244 mg, 3.75 mmol). The mixture was heated at 80° C. for 1 h. After cooling, the mixture was diluted with water and EtOAc. The layers were separated and the aqueous was extracted with EtOAc (2×) and the combined organics washed with water, brine, dried (sodium sulfate) and concentrated to provide crude methyl 2-(6-(1H-tetrazol-1-yl)pyridazin-3-yl)acetate (LC-MS (IE, m/z): 193 [M+1-28]+). The crude ester was dissolved in THF (5.0 mL) and treated with 1 N LiOH (3.75 mL) and the resulting mixture was stirred for 1 h. The resulting mixture was concentrated in vacuo and the resulting powder dried under high vacuum to provide title compound which was used directly in the next step without further purification. LC-MS (IE, m/z): 173 [M+1-28]+.

Provenance & Evidence