Monoperoxyphthalic Acid Magnesium Salt → HCID 53764545, compound

HRID 1532509Notes

Reaction equation

HRID 1532509 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([N:28]([CH3:37])[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].C1C=C(C([O-])=[O:46])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([N:28]([CH3:37])[C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N+:19]([O-:46])=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 21251044HCID 21251044, compound

Product 1

HCID 53764545HCID 53764545, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-[3,4-bis(difluoromethoxy)phenyl]-2-[6-(N-methyl-N-4-methoxyphenylamino)3-pyridyl]ethyl}pyridine from Example 112 (60 mg, 0.11 mmol) in a mixture of 3.0 mL of CH2Cl2 and 0.3 mL MeOH, was added 84 mg (0.136 mmol) of 80% MMPP. Reaction was stirred for 24 h at room temperature, quenched with a saturated solution of NaHCO3 and diluted with ethyl acetate. The organic layer was then washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Gradient 40% to 50% EtOH/ethyl acetate) to afford 27 mg (45%) of the title compound

Workup

  1. customReaction
  2. customquenched with a saturated solution of NaHCO3
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was then washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (Gradient 40% to 50% EtOH/ethyl acetate)

Sources & evidence

ORD record
ord-b1a4667b5566454fbe6d1a7482eb2556
Source dataset
uspto-grants-2001_03
Patent number
US06200993B1

Reaction notes

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