Lithium Hydroxide → HCID 89618834, compound

HRID 1502166Notes

Reaction equation

HRID 1502166 reaction equation
[N:1]1([C:6]2[N:11]=[N:10][C:9]([CH2:12][C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[Li+].[OH-]>C1COCC1>[N:1]1([C:6]2[N:11]=[N:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89619112HCID 89619112, compound

Product 1

HCID 89618834HCID 89618834, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe resulting powder dried under high vacuum

Sources & evidence

ORD record
ord-1e9f670f365643be8aad39c96e053167
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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