m-Chloroperbenzoic acid → HCID 3010656, compound

HRID 2229335Notes

Reaction equation

HRID 2229335 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])[NH:17][C:16]2[C:39]([CH3:43])=[CH:40][CH:41]=[N:42][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])[NH:17][C:16]2[C:39]([CH3:43])=[CH:40][CH:41]=[N:42][C:15]1=2)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3010652HCID 3010652, compound

Product 1

HCID 3010656HCID 3010656, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solid mCPBA (163 mg, 0.75 mmol) was added to a solution of 5,11-dihydro-11-ethyl-4-methyl-8-{2-(4-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (144 mg, 0.34 mmol) in CH2Cl2 (7.5 mL). The solution was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2 (125 mL), washed successively with aqueous 10% Na2S2O3 (2×25 mL), aqueous saturated NaHCO3 (2×25 mL) and brine (25 mL), then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:MeOH, 10:1) to give the title compound (102 mg, 68% yield) as a white solid: MS (ESI) m/z 442 (MH)+.

Workup

  1. washwashed successively with aqueous 10% Na2S2O3 (2×25 mL), aqueous saturated NaHCO3 (2×25 mL) and brine (25 mL)
  2. dry with materialwas dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (CH2Cl2:MeOH, 10:1)

Sources & evidence

ORD record
ord-df3a3e3a3239419cab657f533d060f5b
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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