m-Chloroperbenzoic acid → HCID 3010670, compound

HRID 2229343Notes

Reaction equation

HRID 2229343 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH3:44])[C:18](=[O:43])[C:19]3[CH:29]=[C:28]([CH2:30][CH2:31][O:32][C:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N:36]=[CH:35][CH:34]=4)[CH:27]=[N:26][C:20]=3[N:21]([CH2:24][CH3:25])[C:22]=2[N:23]=1>C(Cl)Cl>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH3:44])[C:18](=[O:43])[C:19]3[CH:29]=[C:28]([CH2:30][CH2:31][O:32][C:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N+:36]([O-:9])=[CH:35][CH:34]=4)[CH:27]=[N:26][C:20]=3[N:21]([CH2:24][CH3:25])[C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69550911HCID 69550911, compound

Product 1

HCID 3010670HCID 3010670, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solid mCPBA (80-85%, m-chloroperbenzoic acid) (60 mg, 0.28 mmol) was added to a solution of 5,11-dihydro-2,5-dimethyl-11-ethyl-8-{2-(4-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (55 mg, 0.13 mmol) in CH2Cl2 (1.3 mL) at room temperature. The mixture was stirred at room temperature for 2.5 h then diluted with CH2Cl2. The resulting solution was successively washed with aqueous 10% Na2S2O3, aqueous saturated NaHCO3 and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (MeOH/EtOAc,2% to 5%) to give the title compound (59 mg, 99% yield) as a white solid: MS (ES) m/z 456 (MH)+.

Workup

  1. washThe resulting solution was successively washed with aqueous 10% Na2S2O3, aqueous saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (MeOH/EtOAc,2% to 5%)

Sources & evidence

ORD record
ord-643f27d13ec541299a530bc376f11f09
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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