Hydrochloric Acid → HCID 135771987, compound

HRID 1511820Notes

Reaction equation

HRID 1511820 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:18]=1)=[N:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[CH:9][N:10]=2.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20].Cl.[OH-].[K+]>N1C=CC=CC=1.O>[CH2:19]([NH:21][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:18]=1)=[N:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[CH:9][N:10]=2)=[O:23])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8022Ethyl isocyanate2×HCID 14797Potassium HydroxideHCID 1363686714-(6-Aminopyrido[2,3-b]pyrazin-3-yl)phenol

Product 1

HCID 135771987HCID 135771987, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

0.50 g of 4-(6-aminopyrido[2,3-b]pyrazin-3-yl)phenol (2.10 mmol) were initially charged in 5.0 ml of pyridine. 183 μl of ethyl isocyanate (2.31 mmol) were added dropwise at room temperature and the mixture was heated to 70-80° C. for 2 h. Thereafter, another 183 μl of ethyl isocyanate were added and the mixture was heated to 70-80° C. for a further 2 h. Once the reaction had ended, the reaction mixture was added to ice-water and neutralized with 1N hydrochloric acid. The precipitated product was filtered off with suction and dried. The product which had been filtered was partly dissolved in ethanol and admixed with 52 mg of potassium hydroxide (0.93 mmol), dissolved in water. The mixture was heated to 40° C. for approx. 1 h. Thereafter, the reaction solution was neutralized with 1N hydrochloric acid and the solvent was removed under reduced pressure. The resulting solid was purified by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

Workup

  1. temperaturethe mixture was heated to 70-80° C. for a further 2 h
  2. filtrationThe precipitated product was filtered off with suction
  3. customdried
  4. filtrationThe product which had been filtered
  5. dissolutionwas partly dissolved in ethanol
  6. temperatureThe mixture was heated to 40° C. for approx. 1 h
  7. customthe solvent was removed under reduced pressure
  8. customThe resulting solid was purified by column chromatography on silica gel (dichloromethane/methanol eluent)
  9. customThis gave a yellow solid

Sources & evidence

ORD record
ord-035a43a892a842b88ab1283e8317f8ac
Source dataset
uspto-grants-2012_07
Patent number
US08217042B2

Reaction notes

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