N-(2-aminoethyl)acetamide → HCID 22118686, compound

HRID 1274984Notes

Reaction equation

HRID 1274984 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:9]([NH:12][CH2:13][CH2:14][NH2:15])(=[O:11])[CH3:10].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:9]([NH:12][CH2:13][CH2:14][NH:15][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 2272543-Chloro-6-methylpyridazineHCID 516892Sodium Bicarbonate

Product 1

HCID 22118686HCID 22118686, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chloro-6-methylpyridazine (1.29 g, 10 mmol), N-(acetyl)ethylenediamine (638 mg, 6.25 mmol) and NaHCO3 (1.6 g) in dry DMF (10 mL) was heated at reflux under argon for 20 h. The mixture was filtered, the filtrate concentrated, and the residue was dissolved in CH2Cl2 and purified by flash chromatography (silica gel, step gradient, 0-8% CH3OH/CH2Cl2) to yield the title compound as a yellow solid (700 mg, 44%): MS (ES) m/e 195.0 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 20 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated
  5. dissolutionthe residue was dissolved in CH2Cl2
  6. custompurified by flash chromatography (silica gel, step gradient, 0-8% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-d6ba2e772d99404395df058f2e7ae805
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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