Pyridazine → HCID 178518814, compound

HRID 927140Notes

Reaction equation

HRID 927140 reaction equation
N1C=CC=CN=1.C([O:14][C:15]1[N:16]=[N:17][C:18]([C:29]#[C:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)=[CH:19][C:20]=1[O:21]CC1C=CC=CC=1)C1C=CC=CC=1>C(OCC)(=O)C>[Cl:37][C:33]1[CH:32]=[C:31]([CH2:30][CH2:29][C:18]2[CH:19]=[C:20]([OH:21])[C:15](=[O:14])[NH:16][N:17]=2)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 9259PyridazineHCID 712699503,4-Bis(benzyloxy)-6-((3-chlorophenyl)ethynyl)pyridazine

Product 1

HCID 178518814HCID 178518814, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-[(3-chloromethyl)phenyl)ethynyl]pyridazine (Intermediate 24) except that the reaction was carried out in ethyl acetate. The crude material was purified by reverse phase chromatography (50 g C18) cartridge eluting with 5-100% acetonitrile/water with acidic modifier and the appropriate fractions combined to give an orange solid. This was recrystallised from ethyl acetate to give a white solid (yield=32%).

Workup

  1. customPrepared
  2. customThe crude material was purified by reverse phase chromatography (50 g C18) cartridge
  3. washeluting with 5-100% acetonitrile/water with acidic modifier
  4. customto give an orange solid
  5. customThis was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-593ba4ed535f4d0587bb8c21251a75df
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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