m-Chloroperbenzoic acid → HCID 67041399, compound

HRID 606077Notes

Reaction equation

HRID 606077 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH:31]=2)[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH3:13]>ClCCl>[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[CH:31]=2)[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]([O-:9])=[CH:20][C:19]=2[N:28]=1)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 67041491HCID 67041491, compound

Product 1

HCID 67041399HCID 67041399, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (1.7 g of 75% pure material) was added to a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridine (1.74 g, 4.31 mmol) in dichloromethane (50 mL). The reaction was stirred at room temperature for 30 minutes; an analysis by TLC then indicated the presence of starting material. Additional mCPBA (0.25 g of 75%) was added, and the reaction was stirred for another 30 minutes and found to be complete. The solvent was removed under reduced pressure, and the residue was triturated with diethyl ether and isolated by filtration to provide 1.64 g of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine as a pale yellow solid.

Workup

  1. stirringthe reaction was stirred for another 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was triturated with diethyl ether
  4. customisolated by filtration

Sources & evidence

ORD record
ord-9827e6eab8034bf6a29eeb233f5369b5
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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