Ethanol → HCID 19081373, compound

HRID 963188Notes

Reaction equation

HRID 963188 reaction equation
C(O)C.[C:4]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11](Cl)[CH:10]=[N:9]1)([CH3:7])([CH3:6])[CH3:5].C(N(CC)CC)C.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][CH:26]=1>CO.C(OCC)(=O)C>[C:4]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11]([NH:32][CH2:31][C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)[CH:10]=[N:9]1)([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 19081414HCID 19081414, compound

Product 1

HCID 19081373HCID 19081373, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 30 ml of ethanol solution of 2.1 g of 2-tert-butyl-5-chloro-4-cyanopyridazin-3-(2H)-one and 1.0 g of triethylamine, 1.1 g of 4-picolylamine was dropwise added under cooling with ice over a period of 5 minutes. Then, the mixture was stirred at room temperature for two hours and then concentrated. The mixture was extracted with ethyl acetate, and the extract was washed twice with a saturated sodium chloride aqueous solution and then dried. Ethyl acetate was distilled off under reduced pressure, and the residue thereby obtained was subjected to column chromatography. Using an eluent (ethyl acetate:methanol=20:1), 2.5 g of the desired product (Compound No. 21) having a melting point of from 174 to 175° C., was obtained.

Workup

  1. temperatureunder cooling with ice over a period of 5 minutes
  2. concentrationconcentrated
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed twice with a saturated sodium chloride aqueous solution
  5. customdried
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe residue thereby obtained

Sources & evidence

ORD record
ord-0c7fd0657cca45789a553115c49303b7
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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