HCID 67440464, compound → HCID 67442053, compound

HRID 1801364Notes

Reaction equation

HRID 1801364 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([C:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28][CH3:29])=[O:27])[CH:20]=3)[N:15]=2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28][CH3:29])=[O:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67440464HCID 67440464, compound

Product 1

HCID 67442053HCID 67442053, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (245 mg, 0.59 mmol) in methanol (5 mL) was added 10% Pd/C (130 mg). The mixture was hydrogenated by a H2 balloon. After filtration, the filtrated was concentrated and purified on preparative Thin layer chromatography to afford 120 mg of methyl 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as syrup. (Yield: 28%, three steps.)

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrated was concentrated
  3. custompurified on preparative Thin layer chromatography

Sources & evidence

ORD record
ord-8e8280dd053647f0bb79e865c5a3c253
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…