Urea → HCID 86678205, compound

HRID 1747554Notes

Reaction equation

HRID 1747554 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:15]([F:18])([F:17])[F:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8](N)=[CH:7][CH:6]=2.N([O-])=O.[Na+].NC(N)=O.[I-:33].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>Cl.O>[Cl:1][C:2]1[C:3]([O:13][CH:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:15]([F:18])([F:17])[F:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([I:33])=[CH:7][CH:6]=2

Participants

9

Reactant 6

HCID 1176UreaHCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 86678204HCID 86678204, compound

Product 1

HCID 86678205HCID 86678205, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In 2.0 mol/L hydrochloric acid (50.0 mL) was dissolved 3-chloro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline-6-amine (2.00 g, 5.64 mmol) obtained in Step 3 and the mixture was cooled to 0° C. Sodium nitrite (506 mg, 7.33 mmol) was added and the mixture was stirred at 0° C. for 10 minutes. Urea (508 mg, 8.46 mmol) was added to the reaction mixture and the mixture was stirred at 0° C. for 10 minutes. Potassium iodide (2.34 g, 14.1 mmol) dissolved in water (10.0 mL) was slowly added and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2) to give Compound A47 (868 mg, 33% yield).

Workup

  1. stirringthe mixture was stirred at 0° C. for 10 minutes
  2. additionwas slowly added
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. extractionExtraction with ethyl acetate
  5. washwashing with saturated brine
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent in the filtrate was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2)
  10. customto give Compound A47 (868 mg, 33% yield)

Sources & evidence

ORD record
ord-1333e7a69d80476c89e1304416c59ade
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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