m-Chloroperbenzoic acid → HCID 3010654, compound

HRID 2229334Notes

Reaction equation

HRID 2229334 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH3:45])[C:18](=[O:44])[C:19]3[CH:30]=[C:29]([CH2:31][CH2:32][O:33][C:34]4[C:43]5[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=5)[N:37]=[CH:36][CH:35]=4)[CH:28]=[N:27][C:20]=3[N:21]([CH:24]3[CH2:26][CH2:25]3)[C:22]=2[N:23]=1>C(Cl)Cl.C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH3:45])[C:18](=[O:44])[C:19]3[CH:30]=[C:29]([CH2:31][CH2:32][O:33][C:34]4[C:43]5[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=5)[N+:37]([O-:9])=[CH:36][CH:35]=4)[CH:28]=[N:27][C:20]=3[N:21]([CH:24]3[CH2:26][CH2:25]3)[C:22]=2[N:23]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3010650HCID 3010650, compound

Product 1

HCID 3010654HCID 3010654, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Solid mCPBA (177 mg, 0.82 mmol) was added to a solution of 2-chloro-11-cyclopropyl-5,11-dihydro-5-methyl-8-{2-(4-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (143 mg, 0.30 mmol) in CH2Cl2 (3 mL) and THF (3 mL). The mixture was stirred at room temperature for 14 h then was concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL), the solution was successively washed with aqueous 10% Na2S2O3 (3×10 mL), aqueous saturated NaHCO3 (3×10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was partially purified by flash chromatography (EtOAc:MeOH, 95:5 to CH2Cl2:MeOH, 9:1). The impure compound was further purified by reverse phase HPLC (CombiPrep ADS-AQ 50×20 mm, 5 μ, 120 A, 5-100% MeCN+0.10% TFA/water+0.10% TFA in 25 min). The pure fractions were treated with aqueous saturated NaHCO3, extracted with EtOAc and the solution was dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (28.3 mg, 19%) as a white solid: MS (ESI) m/z 488/490 (MH)+.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washthe solution was successively washed with aqueous 10% Na2S2O3 (3×10 mL), aqueous saturated NaHCO3 (3×10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was partially purified by flash chromatography (EtOAc:MeOH, 95:5 to CH2Cl2:MeOH, 9:1)
  8. customThe impure compound was further purified by reverse phase HPLC (CombiPrep ADS-AQ 50×20 mm, 5 μ, 120 A, 5-100% MeCN+0.10% TFA/water+0.10% TFA in 25 min)
  9. additionThe pure fractions were treated with aqueous saturated NaHCO3
  10. extractionextracted with EtOAc
  11. dry with materialthe solution was dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ced06253bad426788865a6c9229fb6f
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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