HCID 67440521, compound → HCID 67440469, compound

HRID 1801388Notes

Reaction equation

HRID 1801388 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[N:4]=[C:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1>CO.O1CCCC1.[Pd]>[CH3:15][O:14][C:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH:3]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:17]=1)[C:2]([CH3:32])([CH3:1])[CH2:11]2)=[O:13]

Participants

5

Reactant 1

HCID 67440521HCID 67440521, compound

Product 1

HCID 67440469HCID 67440469, compoundYield 75.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(N-phenylsulfamoyl)phenyl)-3,4-dihydroquinoline-6-carboxylate (170 mg, 0.38 mmol) and 10% Pd/C (150 mg) in methanol (4 mL) and tetrahydrofuran (5 mL) was hydrogenated by a H2 balloon at 30° C. After filtration, the filtrated was concentrated and purified on preparative thin layer chromatography to afford 130 mg of 3,3-Dimethyl-2-(3-phenylsulfamoyl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester.

Workup

  1. customwas hydrogenated by a H2 balloon at 30° C
  2. filtrationAfter filtration
  3. concentrationthe filtrated was concentrated
  4. custompurified on preparative thin layer chromatography

Sources & evidence

ORD record
ord-944b2659db9f46b3a745722c5549d72e
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…