HCID 86677042, compound → HCID 178518834, compound

HRID 927185Notes

Reaction equation

HRID 927185 reaction equation
OC1C(=O)NN=C(CCC2C=CC=CC=2)C=1.C([O:24][C:25]1[N:26]=[N:27][C:28](/[CH:39]=[CH:40]/[C:41]2[CH:46]=[C:45]([F:47])[C:44]([C:48]([F:51])([F:50])[F:49])=[C:43]([F:52])[CH:42]=2)=[CH:29][C:30]=1[O:31]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[F:52][C:43]1[CH:42]=[C:41]([CH2:40][CH2:39][C:28]2[CH:29]=[C:30]([OH:31])[C:25](=[O:24])[NH:26][N:27]=2)[CH:46]=[C:45]([F:47])[C:44]=1[C:48]([F:49])([F:50])[F:51]

Participants

4

Reactant 2

HCID 86677042HCID 86677042, compound2×HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

Product 1

HCID 178518834HCID 178518834, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenylethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-[(E)-2-[3,5-difluoro-4-(trifluoromethyl)phenyl]ethenyl]-pyridazine (Intermediate 77) except that THF was used as the solvent. The crude product was purified by reverse phase chromatography (silica, eluting with 5-100% acetonitrile in water with acid modifier) to afford a white solid, which was recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate to afford 6-{2-[3,5-difluoro-4-(trifluoromethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-one as a white solid (0.079 g, 10%).

Workup

  1. customPrepared
  2. customThe crude product was purified by reverse phase chromatography (silica, eluting with 5-100% acetonitrile in water with acid modifier)
  3. customto afford a white solid, which
  4. customwas recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate

Sources & evidence

ORD record
ord-894fb33ab114455b99251dba3c11a44d
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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