HCID 67441456, compound → HCID 67442598, compound

HRID 1801382Notes

Reaction equation

HRID 1801382 reaction equation
[CH3:1][C:2]1([CH3:27])[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:26])(=[O:25])[NH:23][CH3:24])[CH:17]=1>CO.O1CCCC1>[CH3:1][C:2]1([CH3:27])[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:26])(=[O:25])[NH:23][CH3:24])[CH:17]=1

Participants

3

Reactant 1

HCID 67441456HCID 67441456, compound

Product 1

HCID 67442598HCID 67442598, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(N-methylsulfamoyl)phenyl)-3,4-dihydroquinoline-6-carboxylate (175 mg, 0.438 mmol) in methanol/tetrahydrofuran (9.5 mL/9.5 mL) was treated with H2 at room temperature overnight. LC-MS showed the reaction was complete. The mixture was separated by filtration and the filtrate was concentrate in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to give 143.2 mg of methyl 3,3-dimethyl-2-(3-(N-methylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate, yield: 81.2%.

Workup

  1. additionwas treated with H2 at room temperature overnight
  2. customThe mixture was separated by filtration
  3. concentrationthe filtrate was concentrate in vacuo
  4. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-35b7304f20454ee2818faf1d194243ab
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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