Sulfuric acid, dipropyl ester → 8-{[2-(tert-Butoxycarbonyl-isopropyl-amino)-ethyl]-cyclopropyl-sulfamoyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate
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:22]([O:26][C:27]([N:29]([CH:36]([CH3:38])[CH3:37])[CH2:30][CH2:31][NH:32][CH:33]1[CH2:35][CH2:34]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(OS(OCCC)(=O)=O)CC>>[C:22]([O:26][C:27]([N:29]([CH:36]([CH3:38])[CH3:37])[CH2:30][CH2:31][N:32]([CH:33]1[CH2:34][CH2:35]1)[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]=[CH:18][C:8]=3[C:7]=2[CH:6]=1)(=[O:3])=[O:4])=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH2:18]([C:19]([O-:21])=[O:20])[CH2:8][CH3:7]Participants
Reactant 3
Product 1
Procedure
8-{[2-(tert-Butoxycarbonyl-isopropyl-amino)-ethyl]-cyclopropyl-sulfamoyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate is prepared according to synthesis 111, from 326 mg (1 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid and 288 mg (1.2 mmol) of N-tert-butoxycarbonyl-N′-cyclopropyl-N-isopropyl-ethane-1,2-diamine to give, after esterification according to general method C (using di-n-propylsulfate as the dialkylsulfate) and purification by chromatography on silica (eluent cyclohexane/ethyl acetate 1/1 then 1/3), 201 mg (35% in two stages) of 8-{[2-(tert-butoxycarbonyl-isopropyl-amino)-ethyl]-cyclopropyl-sulfamoyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a white solid.
Workup
- customto give
- custompurification by chromatography on silica (eluent cyclohexane/ethyl acetate 1/1
Sources & evidence
- ORD record
- ord-5537cebfe7de4ee4ac74103eb74a3094
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426437B2
Reaction notes
Loading…