3,4-Bis(benzyloxy)-6-{2-[3-(trifluoromethyl)phenyl]ethynyl}pyridazine → HCID 178518813, compound

HRID 927132Notes

Reaction equation

HRID 927132 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]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>CO.O1CCCC1>[OH:15][C:14]1[C:9](=[O:8])[NH:10][N:11]=[C:12]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=2)[CH:13]=1

Participants

4

Reactant 1

HCID 712703353,4-Bis(benzyloxy)-6-{2-[3-(trifluoromethyl)phenyl]ethynyl}pyridazine2×

Product 1

HCID 178518813HCID 178518813, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-{2-[3-(trifluoromethyl)phenyl]ethynyl}pyridazine (Intermediate 15) except that the reaction was carried out in a mixture of methanol and tetrahydrofuran (2:1). The crude material was purified by reverse phase chromatography, eluting with 5-80% acetonitrile/water with a 0.05% formic acid modifier in the water. The crude product was recrystallised from ethanol/heptane to give a white solid (yield=27%).

Workup

  1. customPrepared
  2. customThe crude material was purified by reverse phase chromatography
  3. washeluting with 5-80% acetonitrile/water with a 0.05% formic acid modifier in the water
  4. customThe crude product was recrystallised from ethanol/heptane

Sources & evidence

ORD record
ord-535984ec5a5f471090216dba5f09e04a
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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