Dimethylformamide → HCID 67103761, compound

HRID 2080821Notes

Reaction equation

HRID 2080821 reaction equation
CN(C=O)C.[C:6]([O:10][C:11](=[O:28])[NH: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])([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].I[CH2:32][CH2:33][CH3:34]>C(Cl)(Cl)Cl>[C:6]([O:10][C:11](=[O:28])[NH: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])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 67103536HCID 67103536, compound

Product 1

HCID 67103761HCID 67103761, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A DMF solution (4.0 ml) containing the compound (0.501 g) obtained in Example 46-2 was added with 60% sodium hydride (76.0 mg) and the whole was stirred at room temperature for 30 minutes. The solution was cooled with ice and then 1-iodopropane (0.184 ml) was dropped thereto. The whole was stirred at room temperature for 23 hours. The solvent in the reaction solution was distillated off. The resultant was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous magnesium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (ethyl acetate/chloroform), thereby obtaining the subject compound (0.378 g) as a colorless crystal.

Workup

  1. temperatureThe solution was cooled with ice
  2. stirringThe whole was stirred at room temperature for 23 hours
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling the solvent
  7. customoff was purified through silica gel column chromatography (ethyl acetate/chloroform)

Sources & evidence

ORD record
ord-a7ef4c4c8b7d4f39a02b14e7d275941b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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