Methyl iodide → 4-Amino-3-[(3-dipropylaminomethyl-benzoyl)-methyl-amino]-benzoic acid methyl ester

HRID 2080769Notes

Reaction equation

HRID 2080769 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[CH:14]=2)[CH:5]=1.[H-].[Na+].[CH3:31]I>CN(C=O)C>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N:11]([C:12](=[O:27])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[CH:14]=2)[CH3:31])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 671038094-Amino-3-(3-dipropylaminomethyl-benzoylamino)-benzoic acid methyl ester

Product 1

HCID 671037494-Amino-3-[(3-dipropylaminomethyl-benzoyl)-methyl-amino]-benzoic acid methyl esterYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (380 mg) obtained in Example 18-3 was dissolved in DMF (7.6 ml) and 60% sodium hydride (60.0 mg) was added thereto, and the whole was stirred for 1 hour. After that, methyl iodide (213 mg) was gradually added thereto and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (83.0 mg) as a brown solid.

Workup

  1. stirringthe whole was stirred at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-a79048b067b74347ae059e31456042ea
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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