Water → HCID 59681779, compound

HRID 1394177Notes

Reaction equation

HRID 1394177 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=2)=[N:4][O:5][N:6]=1.[H-].[Na+].Br[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30].O>CN(C=O)C.CCOC(C)=O>[CH2:27]([N:28]([CH2:31][CH3:32])[CH2:29][CH2:30][O:22][C:19]1[CH:20]=[CH:21][C:16]([N:8]2[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=[C:7]2[C:3]2[C:2]([NH2:1])=[N:6][O:5][N:4]=2)=[CH:17][CH:18]=1)[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 706082-Bromo-N,N-diethylethanamineHCID 57721189HCID 57721189, compound

Product 1

HCID 59681779HCID 59681779, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 50 mg the product from Example 38 (0.17 mmols) in 3.4 mL of dry DMF was added 14 mg of NaH (0.34 mmols, 60% suspension in oil). After stirring at ambient temperature for 5 min, 44 mg of 2-bromoethyl-diethylamine (0.17 mmols) was added to the reaction. The reaction was warmed to 60° C. for 16 h. After cooling to room temperature, 1 mL of water was carefully added to the reaction mixture. The mixture was diluted with 20 mL of EtOAc and washed with 2N NaOH (3×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was dissolved in a minimum volume of DMSO and filtered through a 0.45 m acrodisc filter. The resulting solution was purified on the Gilson reverse-phase HPLC. The resulting product was dissolved in a minimum amount of MeOH and treated with excess 1 N HCl in diethylether. The resulting precipitate was collected and washed with diethylether to afford the title product (11 mg, 17%). MS (ES+) m/e 393 [M]+.

Workup

  1. temperatureThe reaction was warmed to 60° C. for 16 h
  2. temperatureAfter cooling to room temperature
  3. washwashed with 2N NaOH (3×10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in a minimum volume of DMSO
  8. filtrationfiltered through a 0.45 m
  9. filtrationacrodisc filter
  10. customThe resulting solution was purified on the Gilson reverse-phase HPLC
  11. dissolutionThe resulting product was dissolved in a minimum amount of MeOH
  12. additiontreated with excess 1 N HCl in diethylether
  13. customThe resulting precipitate was collected
  14. washwashed with diethylether

Sources & evidence

ORD record
ord-b6e9e8ebcbcb4c5781c0458c504dd4df
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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