Sodium hydride → HCID 23155521, compound

HRID 2080846Notes

Reaction equation

HRID 2080846 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[NH:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[H-].[Na+].I[CH2:26][CH2:27][CH3:28]>CN(C=O)C>[N:16]1([CH2:15][CH2:14][CH2:13][CH2:12][C:11]2[N:10]([CH2:26][CH2:27][CH3:28])[C:3]3[CH:4]=[C:5]([C:8]#[N:9])[CH:6]=[CH:7][C:2]=3[N:1]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 23155398HCID 23155398, compound

Product 1

HCID 23155521HCID 23155521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (1.04 g) obtained in Example 61-2 was dissolved in DMF (31.2 ml) and added with 60% sodium hydride (0.166 g) and 1-iodopropane (0.405 ml) while the whole was being stirred under ice-cooling. The solution was warmed to room temperature and stirred for 15 hours. The reaction solution was poured in ice-cold water and subjected to separation/extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was again dissolved in a 4 mol/l hydrogen chloride/dioxane solution (10 ml) and the whole was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and a saturated saline solution. Then, the resultant was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified′through silica gel column chromatography (chloroform), thereby obtaining the subject compound (451.8 mg) as a yellow oily substance.

Workup

  1. temperaturecooling
  2. stirringstirred for 15 hours
  3. additionThe reaction solution was poured in ice-cold water
  4. extractionsubjected to separation/extraction with chloroform
  5. washThe organic layer was washed with a saturated saline solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. dissolutionThe residue was again dissolved in a 4 mol/l hydrogen chloride/dioxane solution (10 ml)
  9. stirringthe whole was stirred at room temperature for 1 hour
  10. concentrationThe reaction solution was concentrated under reduced pressure
  11. dissolutionThe residue was dissolved in chloroform
  12. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  13. dry with materialThen, the resultant was dried with anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-357e9c8bd1b440b8a7151a386990ee93
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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