Sodium Hydroxide → HCID 16065390, compound

HRID 2425511Notes

Reaction equation

HRID 2425511 reaction equation
CS[C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH:31]1C=C(Cl)C=C(C(OO)=O)C=1.[S:42]([O-:46])([O-])(=[O:44])=S.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH3:31][S:42]([C:3]1[C:4]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:46])=[O:44]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 16036824HCID 16036824, compound

Product 1

HCID 16065390HCID 16065390, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a stirring solution of 3-(methylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (1) (40 mg, 0.097 mmol) in CH2Cl2 (1 mL) was added MCPBA (54 mg of 70-75%, 0.23 mmol) and solution allowed to stir for 1 h. Additional MCPBA (10 mg) was added and reaction heated at 40° C. for 1 h., then allowed to cool. Next was added H2O (1 mL) and a few crystals of sodium thiosulfate, CH2Cl2 (3 mL), and 1 N NaOH (2 mL-aqueous). The layers were shaken together, separated, the organics 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 (6 mg) as a white solid. 1H NMR (300 MHz, CDCl3, 65° C.) δ 8.13 (d, J=8.5 Hz, 1H), 7.92-7.76 (m, 2H), 7.59-7.25 (m, 11H), 6.19-6.08 (m, 1H), 5.27-5.15 (m, 1H), 2.96 (s, 3H), 2.28-1.87 (m, 2H), 1.00 (t, J=7.4 Hz, 3H); HRMS m/z 445.1573, calcd 445.1586.

Workup

  1. customreaction
  2. temperatureto cool
  3. stirringThe layers were shaken together
  4. customseparated
  5. dry with materialthe organics dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (0-25% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-8c80fe02c38b48febee7083829c589ff
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

Loading…