3-Fluoro-2-methylaniline → HCID 86627473, compound

HRID 1969947Notes

Reaction equation

HRID 1969947 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[C:24]([CH3:30])=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>>[F:22][C:23]1[C:24]([CH3:30])=[C:25]([NH:26][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:27]=[CH:28][CH:29]=1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 2855533-Fluoro-2-methylanilineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627473HCID 86627473, compoundYield 3.4%

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 63 μL (0.55 mmol) of 3-fluoro-2-methylaniline. After purification by chromatography on silica (eluent dichloromethane/methanol 96/4) then trituration in diethyl ether, 3.5 mg (2%) of 8-(3-fluoro-2-methyl-phenylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

Workup

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

Sources & evidence

ORD record
ord-7a1bfa88f75a4c079955930a65d7b927
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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