Water → HCID 16064397, compound

HRID 2425517Notes

Reaction equation

HRID 2425517 reaction equation
CS[CH2:3][C:4]1[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.[CH:32]1C=C(Cl)C=C(C(OO)=O)C=1.[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+].O>C(Cl)Cl>[CH3:32][S:43]([CH2:3][C:4]1[C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:47])=[O:45]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 16065392HCID 16065392, compound

Product 1

HCID 16064397HCID 16064397, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirring solution of 3-[(methylthio)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (9) (800 mg, 1.87 mmol) at 0° C. was added MCPBA (900 mg, 70-75%, 4.31 mmol), the cooling bath removed, and reaction allowed to stir for 1 h. Additional MCPBA (100 mg) was added and reaction heated briefly to 40° C., then allowed to cool. Sodium thiosulfate (Na2S2O3.5H2O-1.5 g) and H2O (10 mL) were added and suspension stirred vigorously for 10 min., diluted with CH2Cl2, washed with aqueous 0.3 N NaOH, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-25% EtOAc/CH2Cl2) to give the desired product (630 mg, 73% yield) as a solid. 1HNMR (300 MHz, CDCl3, 52° C.) δ 8.12 (d, J=8.4 Hz, 1H), 7.83-7.68 (m, 2H), 7.61 (d, J=7.7 Hz, 2H), 7.56-7.26 (m, 10H), 5.22 (q, J=7.6 Hz, 1H), 4.74 (d, J=12.3 Hz, 2H), 2.31 (s, 3H), 2.20-1.88 (m, 2H), 1.00 (t, J=7.4 Hz, 3H); LCMS: m/z 459 (MH+).

Workup

  1. customthe cooling bath removed
  2. customreaction
  3. customreaction
  4. temperatureto cool
  5. stirringsuspension stirred vigorously for 10 min.
  6. washwashed with aqueous 0.3 N NaOH
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (0-25% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-839587ab0506409fa9e11fdbb49926ea
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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