Cesium carbonate → HCID 57559685, compound

HRID 1723833Notes

Reaction equation

HRID 1723833 reaction equation
[CH3:1][C:2]1[N:3]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:4]=[C:5]2[C:14]3[CH:13]=[C:12]4[CH:15]=[CH:16][CH:17]=[CH:18][C:11]4=[CH:10][C:9]=3[NH:8][C:7](=[O:19])[C:6]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[C:33]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][CH2:42]Br)([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][CH2:42][N:8]1[C:9]2[CH:10]=[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]3=[CH:13][C:14]=2[C:5]2=[N:4][N:3]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2]([CH3:1])=[C:6]2[C:7]1=[O:19])=[O:44])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 135988233HCID 135988233, compound

Product 1

HCID 57559685HCID 57559685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl 3-methyl-4-oxo-4,5-dihydro-2H-benzo[g]pyrazolo[4,3-c]quinoline-2-carboxylate (1-6) (0.1 g, 0.29 mmol, 1.0 equiv) and cesium carbonate (0.50 g, 1.5 mmol, 5.4 equiv) in DMF (5 ml) was added N-(3-bromopropyl)carbamic acid tert-butyl ester (0.12 g, 0.50 mmol, 1.8 equiv) and the reaction was stirred at room temperature. After 20 hours LC/MS indicated the reaction was 55% complete so an additional 120 mg of alkylating agent was added and the reaction was stirred at room temperature for an additional 24 hours. LC/MS indicated the reaction was complete, and the reaction was filtered to remove the base and purified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.05% NH4OH present) to yield tert-butyl 5-{3-[(tert-butoxycarbonyl)amino]propyl}-3-methyl-4-oxo-4,5-dihydro-2H-benzo[g]pyrazolo[4,3-c]quinoline-2-carboxylate (1-7) as a white solid. LRMS m/z (M+H) 507.6 found, 507.3 required.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for an additional 24 hours
  3. filtrationthe reaction was filtered
  4. customto remove the base
  5. custompurified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.05% NH4OH present)

Sources & evidence

ORD record
ord-596c7a2fe2d84202a29ee4436b329603
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

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