3,4-bis(Benzyloxy)-6-[(2,4-difluorophenyl)ethynyl]pyridazine → HCID 178518829, compound

HRID 927137Notes

Reaction equation

HRID 927137 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][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.O1CCCC1>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[CH2:24][CH2:23][C:12]1[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=1

Participants

4

Reactant 1

HCID 712700403,4-bis(Benzyloxy)-6-[(2,4-difluorophenyl)ethynyl]pyridazine2×

Product 1

HCID 178518829HCID 178518829, compoundYield 26%

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-[(2,4-difluorophenyl)ethynyl]pyridazine (Intermediate 21) 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 yellow solid. This was recrystallised from ethanol to give a white solid (yield=26%).

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
  4. customto give a yellow solid
  5. customThis was recrystallised from ethanol

Sources & evidence

ORD record
ord-ea1d270a1ac04887b04ad1b941168072
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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