HCID 86677038, compound → HCID 178426039, compound

HRID 927184Notes

Reaction equation

HRID 927184 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]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][C:42]=2[CH3:51])=[CH:29][C:30]=1[O:31]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[OH:31][C:30]1[C:25](=[O:24])[NH:26][N:27]=[C:28]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:48])[F:50])=[CH:43][C:42]=2[CH3:51])[CH:29]=1

Participants

4

Reactant 2

HCID 86677038HCID 86677038, compound2×HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

Product 1

HCID 178426039HCID 178426039, compoundYield 36%

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-[2-methyl-4-(trifluoromethyl)phenyl]-ethenyl]pyridazine (Intermediate 76) except that THF was used as the solvent. The crude product was purified by reverse phase chromatography, eluting with 5-100% acetonitrile with acid modifier) and then recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate to afford 4-hydroxy-6-{2-[2-methyl-4-(trifluoromethyl)phenyl]ethyl}-2,3-dihydropyridazin-3-one as a white powder (0.23 g, 36%).

Workup

  1. customPrepared
  2. customThe crude product was purified by reverse phase chromatography
  3. washeluting with 5-100% acetonitrile with acid modifier) and
  4. customthen recrystallised from a mixture of methyl tert-butyl ether and ethyl acetate

Sources & evidence

ORD record
ord-52ec2a6de1df471e9252c25002afac3f
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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