HCID 86677027, compound → HCID 178435906, compound

HRID 927174Notes

Reaction equation

HRID 927174 reaction equation
OC1C(=O)NN=C(CCC2C=CC=CC=2)C=1.C([O:24][C:25]1[N:26]=[N:27][C:28]([C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH2:40])=[CH:29][C:30]=1[O:31]CC1C=CC=CC=1)C1C=CC=CC=1>C(OCC)(=O)C>[C:41]1([CH:39]([C:28]2[CH:29]=[C:30]([OH:31])[C:25](=[O:24])[NH:26][N:27]=2)[CH3:40])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 86677027HCID 86677027, compound2×HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

Product 1

HCID 178435906HCID 178435906, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared by the same method as for 4-hydroxy-6-(2-phenylethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine (Intermediate 25) except that upon completion of the reaction the resulting mixture was filtered through Celite washing with ethanol and then concentrated in vacuo to afford an orange solid. This was purified initially by eluting on a reverse phase C18 chromatography column (0-60% methanol in water with an acidic modifier) and upon combining and concentrating the appropriate fractions the crude product was recrystallised from a mixture of ethyl acetate and heptanes to afford a white solid and the final compound was recrystallised from a mixture of ethyl acetate and heptanes (32% yield).

Workup

  1. filtrationwas filtered through Celite
  2. washwashing with ethanol
  3. concentrationconcentrated in vacuo
  4. customto afford an orange solid
  5. customThis was purified initially
  6. washby eluting on a reverse phase C18 chromatography column (0-60% methanol in water with an acidic modifier) and
  7. concentrationconcentrating the appropriate fractions the crude product
  8. customwas recrystallised from a mixture of ethyl acetate and heptanes
  9. customto afford a white solid

Sources & evidence

ORD record
ord-1bf6cfd0617e4c169d143c98c50bcda2
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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