3,4-Bis(benzyloxy)-6-[(3-(difluoromethyl)phenyl)ethynyl]pyridazine → HCID 178518812, compound

HRID 927138Notes

Reaction equation

HRID 927138 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([F:33])[F:32])[CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.O1CCCC1>[F:33][CH:31]([F:32])[C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:12]2[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 712700393,4-Bis(benzyloxy)-6-[(3-(difluoromethyl)phenyl)ethynyl]pyridazine2×

Product 1

HCID 178518812HCID 178518812, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-[(3-(difluoromethyl)phenyl)ethynyl]pyridazine (Intermediate 22) except that the reaction was carried out in a mixture of ethanol and tetrahydrofuran (1:1). The crude material was purified by reverse phase chromatography (25 g C18) cartridge eluting with 5-100% acetonitrile/water with acidic modifier and the appropriate fractions combined to give a pale orange solid (yield=32%).

Workup

  1. customPrepared
  2. customThe crude material was purified by reverse phase chromatography (25 g C18) cartridge
  3. washeluting with 5-100% acetonitrile/water with acidic modifier

Sources & evidence

ORD record
ord-277abe093e2b4531a83d41e9664ee6d5
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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