Triethylamine → HCID 66866322, compound

HRID 2194412Notes

Reaction equation

HRID 2194412 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4]([CH3:14])[N:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH3:13].C(N(CC)CC)C>C(O)C.[Pd]>[CH3:14][N:4]1[C:3](=[O:15])[CH:2]=[C:7]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])[CH:6]=[N:5]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 668649334-chloro-2-methyl-5-(2-methyl-imidazol-1-yl)-2H-pyridazin-3-one

Product 1

HCID 66866322HCID 66866322, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3.30 g (14.7 mmol) of 4-chloro-2-methyl-5-(2-methyl-imidazol-1-yl)-2H-pyridazin-3-one in 60 ml of ethanol at 50° C. were added 2.44 ml (1.78 g, 17.6 mmol) of triethylamine and 0.312 g of Pd 10%/C. The suspension was stirred under hydrogen atmosphere for 15 h at 50° C. The catalyst was filtered off and washed twice with 10 ml of ethanol. The filtrate was concentrated in vaccuo, and taken up in 50 ml of methylene chloride. The organic phase was washed four times with water, dried and concentrated to yield the title compound (2.30 g, 12.09 mmol, 82%) as a white crystalline solid, MS: m/e=191.2 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed twice with 10 ml of ethanol
  3. concentrationThe filtrate was concentrated in vaccuo
  4. washThe organic phase was washed four times with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8dbf26cd37f442459f189d21d49ad45f
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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