HCID 67442652, compound → HCID 67440754, compound

HRID 1801391Notes

Reaction equation

HRID 1801391 reaction equation
[CH3:1][N:2]([CH3:28])[S:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]([O:26][CH3:27])=[O:25])[CH:18]=3)[N:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]>CO.O1CCCC1.[Pd]>[CH3:28][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]([O:26][CH3:27])=[O:25])[CH:18]=3)[NH:13]2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

5

Reactant 1

HCID 67442652HCID 67442652, compound

Product 1

HCID 67440754HCID 67440754, compoundYield 79.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(3-(N,N-dimethylsulfamoyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (100 mg, 0.25 mmol) and 10% Pd/C (100 mg) in methanol (3 mL) and tetrahydrofuran (3 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 80 mg of methyl 2-(3-(N,N-dimethylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a crude product.

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-0063c4c7ba5340508a6ae0b04da81376
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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