1-Hydroxybenzotriazole → HCID 23369814, compound

HRID 1900765Notes

Reaction equation

HRID 1900765 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.[C:18]([O:22][C:23]([N:25]([CH3:30])[CH2:26][C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[C:18]([O:22][C:23]([N:25]([CH3:30])[CH2:26][C:27]([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:28])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 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 23369814HCID 23369814, compoundYield 69.7%

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, N-tert-butoxycarbonyl-N-methylglycine (2.0 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 extracted with chloroform after the pH was turned to acidic with HCl. The organic phase was washed with saturated aqueous NaCl solution, and dried. The solvent was distilled off under reduced pressure. The resultant residue was recrystallized from chloroform--methanol--ether. As a result, 2.8 g of the title compound was obtained as colorless powdery crystals (69.0%)

Workup

  1. temperaturewhile being cooled on ice
  2. distillationThe reaction mixture was subjected to distillation under reduced pressure
  3. extractionThe resultant residue was extracted with chloroform after the pH
  4. washThe organic phase was washed with saturated aqueous NaCl solution
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-bb3f3a3b3e50474a9eb64599145e2af1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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