m-Chloroperbenzoic acid → HCID 86681231, compound

HRID 1848258Notes

Reaction equation

HRID 1848258 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][N:13]3[CH:18]=[CH:17][N:16]=[C:15]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:14]3=[O:25])[CH:9]=[CH:8][C:6]=2[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][N:13]3[CH:18]=[CH:17][N:16]=[C:15]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:14]3=[O:25])[CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86681230HCID 86681230, compound

Product 1

HCID 86681231HCID 86681231, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-morpholinopyrazin-2(1H)-one (752 mg, 2.0 mmol) and m-CPBA (449 mg, 2.6 mmol) in DCM (20 mL) was stirred at 0° C. for 4 h. The reaction mixture was washed with aqueous Na2S2O3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 1:3 petroleum ether/ethyl acetate to give 1-((2-(methylsulfinyl)benzo[d]thiazol-6-yl)methyl)-3-morpholinopyrazin-2(1H)-one as a light yellow solid (430 mg, 55.1%). 1H NMR (300 MHz, DMSO-d6) δ 8.20 (s, 1H), 8.08 (d, J=8.4 Hz, 1H), 7.59 (d, J=6.9 Hz, 1H), 7.29 (d, J=4.5 Hz, 1H), 6.96 (d, J=4.2 Hz, 1H), 5.20 (s, 2H), 3.65 (s, 8H), 3.07 (s, 3H). LCMS (ESI) m/z 391 (M+H)+.

Workup

  1. washThe reaction mixture was washed with aqueous Na2S2O3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 1:3 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-e99546d3093e4071a2086964b26544c4
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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