Water → HCID 86627572, compound

HRID 1970064Notes

Reaction equation

HRID 1970064 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:22]=[CH:21][C:20]2[NH:19][C:18](=[O:23])[C:17]3[NH:24][CH:25]=[CH:26][C:16]=3[C:15]=2[CH:14]=1.[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28].O>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:22]=[CH:21][C:20]2[NH:19][C:18](=[O:23])[C:17]3[NH:24][CH:25]=[CH:26][C:16]=3[C:15]=2[CH:14]=1)(=[O:4])=[O:3].[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 86627570HCID 86627570, compound

Product 1

HCID 86627572HCID 86627572, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

24 μL (0.3 mmol) of methanesulfonyl chloride is added to a solution of 70 mg (0.2 mmol) of 8-(2-aminophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 0.3 mL of anhydrous pyridine. The solution is stirred at room temperature for 4 hours then water is added. The compound is extracted with ethyl acetate. The organic phases are washed with an aqueous solution of copper sulfate, dried over magnesium sulfate, filtered and evaporated to give 22 mg (25%) of 8-(2-methanesulfonylaminophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. extractionThe compound is extracted with ethyl acetate
  2. washThe organic phases are washed with an aqueous solution of copper sulfate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-406e5adc30b4491aa7e8c4f2db301429
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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