HCID 67442632, compound → HCID 67443241, compound

HRID 1801385Notes

Reaction equation

HRID 1801385 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][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1>CO.O1CCCC1.[Pd]>[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)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1

Participants

5

Reactant 1

HCID 67442632HCID 67442632, compound

Product 1

HCID 67443241HCID 67443241, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(N-(1-methylpyrrolidin-3-yl)sulfamoyl)phenyl)-3,4-dihydroquinoline-6-carboxylate (152 mg, 0.33 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 140 mg of methyl 3,3-dimethyl-2-(3-(N-(1-methylpyrrolidin-3-yl)sulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white solid. (Yield: 92%).

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-6ebe93f5552c45bd8f8516ebef7fce54
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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