m-Chloroperbenzoic acid → HCID 23119571, compound

HRID 2229351Notes

Reaction equation

HRID 2229351 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([N:14]1[C:20]2[N:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=[CH:30][CH:29]=3)=[CH:24][C:19]=2[C:18](=[O:38])[N:17]([CH3:39])[C:16]2[CH:40]=[CH:41][C:42]([C:44]([F:47])([F:46])[F:45])=[N:43][C:15]1=2)[CH3:13]>C(Cl)Cl>[CH2:12]([N:14]1[C:20]2[N:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N+:31]([O-:9])=[CH:30][CH:29]=3)=[CH:24][C:19]=2[C:18](=[O:38])[N:17]([CH3:39])[C:16]2[CH:40]=[CH:41][C:42]([C:44]([F:46])([F:45])[F:47])=[N:43][C:15]1=2)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18466634HCID 18466634, compound

Product 1

HCID 23119571HCID 23119571, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solid mCPBA (80-85%, m-chloroperbenzoic acid) (16 mg, 0.08 mmol) was added to a solution of 5,11-dihydro-11-ethyl-5-methyl-8-{2-(4-quinolinyloxy)ethyl}-2-(trifluoromethyl)-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (22 mg, 0.04 mmol) in CH2Cl2 (0.5 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:CHCl3, 5% to 10%) to give the title compound (11 mg, 52% yield) as a white solid: MS (ESI) m/z 511 (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:CHCl3, 5% to 10%)

Sources & evidence

ORD record
ord-6f4078e17da744e9a7e71c9ddee47890
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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