m-Toluidine → HCID 86627462, compound

HRID 1969936Notes

Reaction equation

HRID 1969936 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].[CH3:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>>[O:15]=[C:10]1[C:9]2[NH:16][CH:17]=[CH:18][C:8]=2[C:7]2[CH:6]=[C:5]([S:2](=[O:3])(=[O:4])[NH:26][C:25]3[CH:24]=[C:23]([CH3:22])[CH:29]=[CH:28][CH:27]=3)[CH:14]=[CH:13][C:12]=2[NH:11]1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627462HCID 86627462, compoundYield 45.9%

Procedure

This compound is prepared according to synthesis 25, from 150 mg (0.46 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 2) and 59 μL (0.55 mmol) of 3-methylaniline. After purification by chromatography on silica (eluent dichloromethane/methanol 96/4) then trituration in diethyl ether, 45 mg (23%) of 4-oxo-8-m-tolylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent dichloromethane/methanol 96/4)

Sources & evidence

ORD record
ord-9055e153603c4cc3b70947529af13561
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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