Potassium Carbonate → HCID 22611283, compound

HRID 726383Notes

Reaction equation

HRID 726383 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]2[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]3=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][N:32]1[CH:36]=[C:35]([CH2:37][CH2:38]OS(C)(=O)=O)[CH:34]=[N:33]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]2[CH2:16][CH2:15][CH:14]([NH:22][CH2:38][CH2:37][C:35]4[CH:34]=[N:33][N:32]([CH3:31])[CH:36]=4)[CH2:13][C:12]3=2)=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15289310HCID 15289310, compound2×HCID 22611188HCID 22611188, compound

Product 1

HCID 22611283HCID 22611283, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
150 °C

Procedure

To a mixture of 0.40 gm (1.24 mMol) 6-(4-fluorobenzoyl)amino-3-amino-1,2,3,4-tetrahydro-9H-carbazole and 0.257 gm (1.86 mMol) potassium carbonate in 8.0 mL dimethylform-amide were added 0.303 gm (1.49 mMol) 2-(1-methyl-1H-pyrazol-4-yl)-1-mesyloxyethane in 2.0 mL dimethylformamide and the mixture was stirred at 60°-75° C. for 18 hours. An additional 0.101 gm (0.50 mMol) 2-(1-methyl-1H-pyrazol-4-yl)-1-mesyloxyethane were added and the reaction heated to 150° C. After 1.5 hours the reaction mixture was cooled to room temperature and was then partitioned between water and dichloromethane. The aqueous phase was extracted again with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 95:5:0.5 dichloromethane:methanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.180 gm (33.6%) of 6-(4-fluorobenzoyl)amino-3-(2-(1-methyl-1H-pyrazol-4-yl)ethyl)amino-1,2,3,4-tetrahydro-9H-carbazole. The corresponding hydrochloride salt was prepared to provide the title compound.

Workup

  1. temperatureAfter 1.5 hours the reaction mixture was cooled to room temperature
  2. customwas then partitioned between water and dichloromethane
  3. extractionThe aqueous phase was extracted again with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with 95:5:0.5 dichloromethane
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4a6869dcbe44b78b5e8a93e666737b1
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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