4-Fluoro-N-methylaniline → HCID 86627470, compound

HRID 1969944Notes

Reaction equation

HRID 1969944 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].[F:22][C:23]1[CH:30]=[CH:29][C:26]([NH:27][CH3:28])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:30]=[CH:29][C:26]([N:27]([CH3:28])[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:25][CH:24]=1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 680244-Fluoro-N-methylanilineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627470HCID 86627470, compoundYield 24.5%

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 62 μL (0.55 mmol) of (4-fluoro)-N-methyl-aniline. After purification by chromatography on silica (eluent dichloromethane/methanol 95/5) then trituration in methanol, 25 mg (12%) of 8-[(4-fluorophenyl)-methyl-sulfamoyl)-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 95/5)

Sources & evidence

ORD record
ord-0929b29dcd1744c6972d9481b57b1bb0
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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