Water → HCID 67103581, compound

HRID 2080829Notes

Reaction equation

HRID 2080829 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:27])[NH:17][C:18]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:19]=1[NH2:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:32][CH2:33][CH3:34].O>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:27])[N:17]([C:18]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:19]=1[NH2:26])[CH2:32][CH2:33][CH3:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 67103490HCID 67103490, compound

Product 1

HCID 67103581HCID 67103581, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The compound (961 mg) obtained in Example 48-1 was dissolved in DMF (20 ml). After having been cooled to 0° C., the solution was added with 60% sodium hydride (72.9 mg) and warmed back to room temperature and the whole was stirred for 30 minutes. 1-Iodopropane (0.30 ml) was dropped to the solution and the whole was stirred for additional 3 hours. After having been cooled to 0° C., the solution was added with water to stop the reaction and concentrated. The residue was subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution, and dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (317 mg) as a yellow oily substance.

Workup

  1. temperaturewarmed back to room temperature
  2. stirringthe whole was stirred for additional 3 hours
  3. temperatureAfter having been cooled to 0° C.
  4. customthe reaction
  5. concentrationconcentrated
  6. extractionThe residue was subjected to extraction with chloroform
  7. washThe organic layer was washed with water
  8. dry with materiala saturated saline solution, and dried with anhydrous sodium sulfate
  9. customThe residue obtained
  10. distillationby distilling the solvent
  11. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-eb11a9c382454cfaa089a08b195217fc
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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