1,4-Dioxane hydrochloride → HCID 67103529, compound

HRID 2080770Notes

Reaction equation

HRID 2080770 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N:11]([C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[CH:15]=2)[CH3:12])[CH:5]=1.Cl.O1CCOCC1>CO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[CH:15]=3)[N:11]([CH3:12])[C:6]=2[CH:5]=1)=[O:29]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 671037494-Amino-3-[(3-dipropylaminomethyl-benzoyl)-methyl-amino]-benzoic acid methyl ester

Product 1

HCID 67103529HCID 67103529, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (83.0 mg) obtained in Example 18-4 was dissolved in methanol (1.0 ml) and added with a 4 mol/l hydrogen chloride/dioxane solution (1.0 ml) and the whole was stirred at room temperature for 6 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in methanol to generate a free compound therefrom through an anion-exchange resin (Amberlite IRA-410). The resin was separated by filtration and the filtrate subjected to distillation of the solvent under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (44.0 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in methanol
  4. customThe resin was separated by filtration
  5. distillationthe filtrate subjected to distillation of the solvent under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-2dc1b11aab784de9a86f7481f16d11c8
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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