1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 56979040, compound

HRID 481764Notes

Reaction equation

HRID 481764 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:28][CH:29]1[C:35](=[O:36])[NH:34][C:33]2[N:37]=[CH:38][CH:39]=[CH:40][C:32]=2[CH2:31][CH2:30]1>CN(C=O)C>[CH3:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:15])[CH2:10][C:11](=[O:13])[NH:28][CH:29]1[C:35](=[O:36])[NH:34][C:33]2[N:37]=[CH:38][CH:39]=[CH:40][C:32]=2[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 19067032HCID 19067032, compound

Product 1

HCID 56979040HCID 56979040, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 68 mg of 3-t-butoxycarbonylamino-3-methylbutanoic acid in 1 mL of DMF was added 60 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). The mixture was stirred at 20° C. for 2 h before 50 mg of 7-amino-5,6,7,9-tetrahydro-8H-pyrido[2,3-b]azepin-8-one was added and the reaction was stirred an additional 18 h. The DMF was removed in vacuo and the residue was purified by preparative silica gel layer chromatography to yield 52 mg of the product characterized by its NMR and mass spectra.

Workup

  1. additionwas added
  2. customThe DMF was removed in vacuo
  3. customthe residue was purified by preparative silica gel layer chromatography

Sources & evidence

ORD record
ord-44b9d83ab4964cac98ef192300d05360
Source dataset
uspto-grants-1998_08
Patent number
US05789587

Reaction notes

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