Benzenamine, 4-(4-morpholinyl)- → HCID 86627479, compound

HRID 1969953Notes

Reaction equation

HRID 1969953 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].[N:22]1([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[N:22]1([C:28]2[CH:29]=[CH:30][C:31]([NH:32][S:2]([C:5]3[CH:14]=[CH:13][C:12]4[NH:11][C:10](=[O:15])[C:9]5[NH:16][CH:17]=[CH:18][C:8]=5[C:7]=4[CH:6]=3)(=[O:3])=[O:4])=[CH:33][CH:34]=2)[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627479HCID 86627479, compoundYield 49.8%

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 98 mg (0.55 mmol) of 4-morpholin-4-yl-aniline. After purification by chromatography on silica (eluent dichloromethane/methanol 95/5) then trituration in methanol, 57 mg (25%) of 8-(4-morpholin-4-yl-phenylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a gray solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-67a7df3988394b8cb5fa495c3d2e9a3e
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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