Hydrochloric Acid → HCID 22079774, compound

HRID 1900764Notes

Reaction equation

HRID 1900764 reaction equation
[NH2:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.Cl.[CH3:19][N:20]([CH3:25])[CH2:21][C:22](O)=[O:23].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH3:19][N:20]([CH3:25])[CH2:21][C:22]([NH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 233695672-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 22079774HCID 22079774, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.3 g, 10 mmol) was dissolved in dimethylformamide (100 ml) while being cooled on ice. To the obtained mixture, a hydrochloric acid salt of N,N-dimethylglycine (1.45 g, 11 mmol), WSC.HCl (2.0 g, 11.0 mmol), and HOBT (1.4 g, 11.0 mmol) were added, and the resultant mixture was stirred at room temperature overnight. The reaction mixture was subjected to distillation under reduced pressure. The resultant residue was recrystallized from ethanol--hexane. As a result, 2.7 g of the title compound was obtained as pale yellow powdery crystals (77.0%)

Workup

  1. temperaturewhile being cooled on ice
  2. distillationThe reaction mixture was subjected to distillation under reduced pressure
  3. customThe resultant residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cff13bd13a484fd6a8d9394594b029c1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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