m-Chloroperbenzoic acid → 5,11-Dihydro-11-ethyl-2-fluoro-5-methyl-8-{2-{(1-oxido-4-quinolinyl)oxy}-ethyl}-6H-dipyrido[3,2-b:2',3'-e] [l,4]diazepin-6-one

HRID 2229333Notes

Reaction equation

HRID 2229333 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F: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>[CH2:24]([N:21]1[C:20]2[N:26]=[CH:27][C:28]([CH2:30][CH2:31][O:32][C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N+:36]([O-:9])=[CH:35][CH:34]=3)=[CH:29][C:19]=2[C:18](=[O:43])[N:17]([CH3:44])[C:16]2[CH:15]=[CH:14][C:13]([F:12])=[N:23][C:22]1=2)[CH3:25]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30106485,11-Dihydro-11-ethyl-2-fluoro-5-methyl-8{2-(4-quinolinyloxy)ethyl}-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 30106555,11-Dihydro-11-ethyl-2-fluoro-5-methyl-8-{2-{(1-oxido-4-quinolinyl)oxy}-ethyl}-6H-dipyrido[3,2-b:2',3'-e] [l,4]diazepin-6-oneYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid mCPBA (457 mg, 2.12 mmol) was added to a solution of 5,11-dihydro-2-fluoro-11-ethyl-5-methyl-8-{2-(4-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (470 mg, 1.06 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 13 h then was concentrated under reduced pressure. The residue was dissolved in CHCl3 (75 mL), the solution was successively washed with aqueous 10% Na2S2O3 (3×25 mL), aqueous saturated NaHCO3 (3×25 mL) and brine (25 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CHCl3:MeOH, 19:1 to 9:1) to give the title compound (250 mg, 51% yield) as a white solid: MS (ESI) m/z 460 (MH)+.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CHCl3 (75 mL)
  3. washthe solution was successively washed with aqueous 10% Na2S2O3 (3×25 mL), aqueous saturated NaHCO3 (3×25 mL) and brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (CHCl3:MeOH, 19:1 to 9:1)

Sources & evidence

ORD record
ord-8857bc6f9cdd41cbb8183e10ba48f826
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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