Triethylamine → HCID 86614913, compound

HRID 2080851Notes

Reaction equation

HRID 2080851 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:29]([N:31](CC)CC)[CH3:30].BrCC#N>CN(C=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:30][C:29]#[N:31])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 86614913HCID 86614913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (522 mg) obtained in Example 23-4 was dissolved in DMF (10 ml) and added with triethylamine (372 μl) and bromoacetonitrile (139 μl) and the whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and added with a saturated aqueous sodium hydrogen carbonate solution and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (469 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. additionadded with a saturated aqueous sodium hydrogen carbonate solution
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washwashed with a saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ba95d1f7fe254b45b56bff81a73b9921
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…