Trimethylamine → HCID 86754297, compound

HRID 583118Notes

Reaction equation

HRID 583118 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[O:25][CH3:26])[CH2:16][NH:17][O:18][CH:19]=[C:20]=[O:21])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Cl:29][C:30]1[C:31](=[O:41])[NH:32][N:33]=[C:34]([O:37][CH:38]([CH3:40])[CH3:39])[C:35]=1Cl.CN(C)C>CO>[Cl:29][C:30]1[C:31](=[O:41])[NH:32][N:33]=[C:34]([O:37][CH:38]([CH3:39])[CH3:40])[C:35]=1[N:17]([O:18][CH:19]=[C:20]=[O:21])[CH2:16][C:15]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:13]([N:10]2[CH2:9][CH2:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[CH:28][CH:27]=3)[CH2:12][CH2:11]2)[CH:14]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 15079011HCID 15079011, compoundHCID 86754298HCID 86754298, compound

Product 1

HCID 86754297HCID 86754297, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture comprising 1.6 g of 3-[4-(4-aminobenzyl)piperazin-1-yl]-carbonylmethoxy-4-methoxybenzylamine, 770 mg of 4,5-dichloro-6-isopropoxy-3(2H)-pyridazinone, 460 mg of trimethylamine and 20 ml of methanol, was refluxed under heating with stirring for 2 days. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. The organic layer was washed with an aqueous potassium carbonate solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→chloroform:methanol=15:1) and then crystallized from diethyl ether to obtain 1.6 g of the above-identified compound as white crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe organic layer was washed with an aqueous potassium carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→chloroform:methanol=15:1)
  9. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-85486e40219445e7b5ecab00f6681310
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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