Potassium Carbonate → HCID 57576034, compound

HRID 1970011Notes

Reaction equation

HRID 1970011 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:47])[S:27]([C:30]2[CH:39]=[CH:38][C:37]3[NH:36][C:35](=[O:40])[C:34]4[NH:41][CH:42]=[C:43]([C:44]([OH:46])=[O:45])[C:33]=4[C:32]=3[CH:31]=2)(=[O:29])=[O:28])=[CH:22][CH:21]=1>CN(C)C=O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:47])[S:27]([C:30]2[CH:39]=[CH:38][C:37]3[NH:36][C:35](=[O:40])[C:34]4[NH:41][CH:42]=[C:43]([C:44]([O:46][CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[O:45])[C:33]=4[C:32]=3[CH:31]=2)(=[O:29])=[O:28])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 57576069HCID 57576069, compound

Product 1

HCID 57576034HCID 57576034, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9 mg (0.04 mmol) of 3-bromo-N-tert-butoxycarbonyl-propylamine and 8 mg (0.06 mmol) of potassium carbonate are added to a solution of 21 mg (0.05 mmol) of 8-[(4-fluorophenyl)-methyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid dissolved in 0.5 mL of dimethylformamide. The reaction mixture is stirred for 18 hours at room temperature then the solvents are evaporated. The residue is purified by chromatography on silica (eluent cyclohexane/ethyl acetate 2/8) then triturated in diethyl ether to give 6 mg (21%) of 3-tert-butoxycarbonylamino-propyl 8-[(4-fluorophenyl)-methyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylate in the form of a white solid.

Workup

  1. customthe solvents are evaporated
  2. customThe residue is purified by chromatography on silica (eluent cyclohexane/ethyl acetate 2/8)
  3. customthen triturated in diethyl ether

Sources & evidence

ORD record
ord-4c5c0dc917014422a360129653fd14d7
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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