Dimethylamine → (3aSR,10RS)-2-(2-Dimethylamino-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

HRID 41027Notes

Reaction equation

HRID 41027 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:29](=[O:30])[N:7]2[CH:8]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=3)[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][C:6]2([CH3:31])[C:5]1=[O:32])=[CH:15][C:14]([O:19][CH2:20][CH3:21])=[CH:13][CH:12]=4.[CH3:33][NH:34][CH3:35].O>C(#N)C.O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:33][N:34]([CH3:35])[CH2:2][CH2:3][N:4]1[C:29](=[O:30])[N:7]2[CH:8]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=3)[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][C:6]2([CH3:31])[C:5]1=[O:32])=[CH:15][C:14]([O:19][CH2:20][CH3:21])=[CH:13][CH:12]=4

Participants

7

Reactant 3

HCID 674Dimethylamine3×HCID 962WaterHCID 68937590(3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

Product 1

HCID 68946359(3aSR,10RS)-2-(2-Dimethylamino-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dioneYield 44%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent3×HCID 10340Sodium CarbonateSolvent

Procedure

To a suspension of 200 mg (3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 22) in 10 ml acetonitrile are added 200 μl of a 2 M solution of dimethyl amine in tetrahydrofurane and 85 mg sodium carbonate. The mixture is heated to reflux and additional 1 ml of the 2 m solution of dimethyl amine in THF are added. After additional 2 h heating to reflux, another 600 μl of the solution of dimethyl amine in THF are added. The mixture is heated to reflux for 15 h. Water is added and the mixture is extracted with ethyl acetate. The combined organic layers are washed with brine and dried with magnesium sulfate. After removal of the solvent under reduced pressure, the residue is triturated with diisopropyl ether. 82 mg (44%) of title compound are obtained as a colorless solid. MS: m/z (MH+)=463.2

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperatureAfter additional 2 h heating
  4. temperatureto reflux
  5. temperatureThe mixture is heated
  6. temperatureto reflux for 15 h
  7. extractionthe mixture is extracted with ethyl acetate
  8. washThe combined organic layers are washed with brine
  9. dry with materialdried with magnesium sulfate
  10. customAfter removal of the solvent under reduced pressure
  11. customthe residue is triturated with diisopropyl ether

Sources & evidence

ORD record
ord-208d6f0919c143c7a2b3fe4286634589
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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