Benzocaine → HCID 86627471, compound

HRID 1969945Notes

Reaction equation

HRID 1969945 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].[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1>>[CH2:30]([O:29][C:27]([C:26]1[CH:25]=[CH:24][C:23]([NH:22][S:2]([C:5]2[CH:14]=[CH:13][C:12]3[NH:11][C:10](=[O:15])[C:9]4[NH:16][CH:17]=[CH:18][C:8]=4[C:7]=3[CH:6]=2)(=[O:3])=[O:4])=[CH:33][CH:32]=1)=[O:28])[CH3:31].[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 2337BenzocaineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627471HCID 86627471, compoundYield 3.6%

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 91 mg (0.55 mmol) of ethyl 4-amino-benzoate. After purification by chromatography on silica (eluent dichloromethane/methanol 96/4) then trituration in methanol, 4 mg (2%) of 8-(4-ethoxycarbonyl-phenylsulfamoyl)-4-oxo-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-c3cf0ff9cb4641379cb02ac744ec97f4
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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