Triethylamine → N-Methoxy-N-methylpyridazine-4-carboxamide

HRID 2092015Notes

Reaction equation

HRID 2092015 reaction equation
Cl.CN[O:4][CH3:5].Cl.C[N:8](C)[CH2:9][CH2:10][CH2:11][N:12]=[C:13]=NCC.[OH2:18].O[N:20]1[C:24]2C=CC=C[C:23]=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH3:5][O:4][N:12]([CH3:13])[C:11]([C:10]1[CH:23]=[CH:24][N:20]=[N:8][CH:9]=1)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 59574572N-Methoxy-N-methylpyridazine-4-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A N,N-dimethylformamide solution (16 mL) of 4-pydirazincarboxylic acid (1.61 g, 13.0 mmol), N-methyl-N-methoxyamine hydrochloride (2.54 g, 26.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.23 g, 32.5 mmol), 1-hydroxybenzotriazole hydrate (catalytic amount) and triethylamine (9.06 mL, 65.0 mmol) was stirred at room temperature for 3 days. After completion of the reaction, the solvent was removed by vacuum distillation, and the residue was mixed with water and chloroform and filtered through celite. The filtrate was extracted with chloroform, and the extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (94% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum distillation
  3. additionthe residue was mixed with water and chloroform
  4. filtrationfiltered through celite
  5. extractionThe filtrate was extracted with chloroform
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3fc17cb8ba0d475d9eae81fa71ecd889
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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