tert-Butyl (4-aminophenyl)carbamate → HCID 86627477, compound

HRID 1969951Notes

Reaction equation

HRID 1969951 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].C(OC([NH:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1)=O)(C)(C)C>>[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][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:32][CH:31]=1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627477HCID 86627477, compoundYield 5.1%

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 115 mg (0.55 mmol) of N-tert-butoxycarbonyl-para-phenylenediamine. After purification by chromatography on silica gel (chloroform/methanol/ammonia 90/25/4) then trituration in diethyl ether, 5 mg (3%) of 8-(4-aminophenylsulfamoyl)-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 gel (chloroform/methanol/ammonia 90/25/4)

Sources & evidence

ORD record
ord-3c0b7cf13de8496c91b0bea915cd80f6
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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