Ethyl orthoformate → HCID 89619112, compound

HRID 1502165Notes

Reaction equation

HRID 1502165 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)(=O)C.O.CCOC(C)=O>[N:1]1([C:2]2[N:7]=[N:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)[CH:13]=[N:25][N:24]=[N:23]1

Participants

7

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 89618850HCID 89618850, compound

Product 1

HCID 89619112HCID 89619112, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

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. temperatureAfter cooling
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with EtOAc (2×)
  4. washthe combined organics washed with water, brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5d037a741694e68be3761949257310b
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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