Ethylenediamine → 6-[6-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-quinoline

HRID 1890953Notes

Reaction equation

HRID 1890953 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[N:28]=[CH:27][CH:26]=[CH:25]5)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[N:8]1.FC(F)(F)C(O)=O.C(N)CN>ClCCl.CO>[NH:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[N:28]=[CH:27][CH:26]=[CH:25]5)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[N:8]1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 689770066-{6-[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl}-quinoline

Product 1

HCID 1359070146-[6-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-quinolineYield 53.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-{6-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl}-quinoline (150 mg, 0.32 mmol) in dichloromethane (8 mL) at 0° C. was added trifluoroacetic acid. After 3 hours the mixture was concentrated to dryness and taken Up in dichloromethane and neutralized via the addition of aqueous NaHCO3. To this emulsion was added a chloroform/methanol (95/5) mixture (20 mL) and brine (30 mL). The organic phase was separated and the organic phase filtered and the solid residue washed with water then Et2O and dried to return a yellow solid (64 mg). This solid was taken up in methanol (2 mL) to which ethylenediamine (1 mmol) was added and heated at 50° C. for 1 hour. The mixture was cooled to ambient temperature and the solid collected via filtration and dried to return title compound as a white solid (57 mg, 0.17 mmol, 53% yield).

Workup

  1. concentrationAfter 3 hours the mixture was concentrated to dryness
  2. additiontaken Up in dichloromethane and neutralized via the addition of aqueous NaHCO3
  3. additionTo this emulsion was added a chloroform/methanol (95/5) mixture (20 mL) and brine (30 mL)
  4. customThe organic phase was separated
  5. filtrationthe organic phase filtered
  6. washthe solid residue washed with water
  7. dry with materialEt2O and dried
  8. additionwas added
  9. temperatureThe mixture was cooled to ambient temperature
  10. filtrationthe solid collected via filtration
  11. customdried

Sources & evidence

ORD record
ord-8b1c83d2441548a4a4071675b832fe2b
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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