Dimethylamine, hydrochloride → HCID 24822200, compound

HRID 72729Notes

Reaction equation

HRID 72729 reaction equation
[CH:1]([C:4]1[N:8]2[C:9]3[C:14]([NH:15][C:16](=[O:17])[C:7]2=[CH:6][N:5]=1)=[CH:13][C:12]([C:18]([OH:20])=O)=[CH:11][CH:10]=3)([CH3:3])[CH3:2].Cl.[CH3:22][NH:23][CH3:24].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH:1]([C:4]1[N:8]2[C:9]3[C:14]([NH:15][C:16](=[O:17])[C:7]2=[CH:6][N:5]=1)=[CH:13][C:12]([C:18]([N:23]([CH3:24])[CH3:22])=[O:20])=[CH:11][CH:10]=3)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 591988671-Isopropyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxyic acid

Product 1

HCID 24822200HCID 24822200, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 1-isopropyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxyic acid as synthesized in above Example 8, 271 mg, dimethylamine hydrochloride 90 mg, 1-hydroxybenzotriazole 230 mg, 4-dimethylaminopyridine 24 mg, pyridine 6.8 mL and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 288 mg was stirred for 18.5 hours in nitrogen atmosphere. After distilling the solvent off, 25 mL of water was added to the residue and heated under reflux. Cooling the reaction liquid off, the precipitated crystals were recovered by filtration and washed successively with water, hexane and then with diethyl ether. Drying the crystals by heating under reduced pressure, 235 mg of the title compound was obtained.

Workup

  1. distillationAfter distilling the solvent off, 25 mL of water
  2. additionwas added to the residue
  3. temperatureheated
  4. temperatureunder reflux
  5. temperatureCooling
  6. customthe reaction liquid off, the precipitated crystals
  7. filtrationwere recovered by filtration
  8. washwashed successively with water, hexane
  9. customDrying the crystals
  10. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-473b10f398574602ac24564bced50c96
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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