m-Chloroperbenzoic acid → HCID 71224273, compound

HRID 2402944Notes

Reaction equation

HRID 2402944 reaction equation
[C:1]([C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11](SC)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O.CCN(C(C)C)C(C)C.[CH3:42][N:43]1[CH2:48][CH2:47][N:46]([C:49]2[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=2)[CH2:45][CH2:44]1>ClCCl>[C:1]([C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]([NH:53][C:52]2[CH:51]=[CH:50][C:49]([N:46]3[CH2:45][CH2:44][N:43]([CH3:42])[CH2:48][CH2:47]3)=[CH:55][CH:54]=2)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 71224526HCID 71224526, compound

Product 1

HCID 71224273HCID 71224273, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a cold (0° C.) solution of Example 3A (200 mg, 0.661 mmol) in dichloromethane (2.2 mL) was added meta-chloroperoxybenzoic acid (179 mg, 0.728 mmol) in a single portion. After 1 hour, the reaction mixture was partitioned between 10% sodium thiosulfate solution and ethyl acetate. The layers were separated, and the organic layer was washed with saturated sodium bicarbonate solution, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (3 mL). Hunig's base (231 μl, 1.323 mmol) and 4-(4-methylpiperazin-1-yl)aniline (127 mg, 0.661 mmol) were added to the solution, and the reaction was heated to 45° C. for 3 hours. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure. The crude residue was purified by MPLC (10 g SiO2), eluting with dichloromethane to 10% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 446.3 [M+H]+.

Workup

  1. customthe reaction mixture was partitioned between 10% sodium thiosulfate solution and ethyl acetate
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in N,N-dimethylformamide (3 mL)
  8. temperatureThe reaction mixture was cooled to room temperature
  9. custompartitioned between water and ethyl acetate
  10. concentrationThe organic layer was concentrated under reduced pressure
  11. customThe crude residue was purified by MPLC (10 g SiO2)
  12. washeluting with dichloromethane to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-1d17ba3c6926403ea8630151102915fa
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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