N,N-Diethylethylenediamine → HCID 58452687, compound

HRID 70596Notes

Reaction equation

HRID 70596 reaction equation
ON1C2C=CC=CC=2N=N1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].Cl.CN(C)CCCN=C=NCC.[CH:31]1(/[CH:36]=[C:37](\[C:48]2[CH:56]=[CH:55][C:51]([C:52](O)=[O:53])=[CH:50][CH:49]=2)/[C:38]2[NH:39][C:40](=[O:47])[C:41]([CH:44]3[CH2:46][CH2:45]3)=[CH:42][CH:43]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1>CN(C)C=O.O.C(N(CC)CC)C>[CH:31]1(/[CH:36]=[C:37](\[C:48]2[CH:56]=[CH:55][C:51]([C:52]([NH:16][CH2:15][CH2:14][N:13]([CH2:17][CH3:18])[CH2:11][CH3:12])=[O:53])=[CH:50][CH:49]=2)/[C:38]2[NH:39][C:40](=[O:47])[C:41]([CH:44]3[CH2:45][CH2:46]3)=[CH:42][CH:43]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

8

Reactant 4

HCID 60993N,N-DiethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67396105HCID 67396105, compound

Product 1

HCID 58452687HCID 58452687, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-Hydroxybenzotriazole (39 mg), triethylamine (0.04 mL), N,N-diethylethylenediamine (0.061 mL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (55 mg) were sequentially added to a solution of 4-[(E)-2-cyclopentyl-1-(5-cyclopropyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]benzoic acid (50 mg) in N,N-dimethylformamide at room temperature, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=20:1) and the resulting solid was washed with diethyl ether to give the title compound as a white solid (17 mg, 26%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative TLC (chloroform:methanol=20:1)
  6. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-ae5d28ac3fc1466e8675b002db48e8e9
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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