1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53866133, compound

HRID 344233Notes

Reaction equation

HRID 344233 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24](O)=[O:25])=[C:22]([O:30][CH3:31])[CH:21]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24]([NH:18][CH2:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]2)=[O:25])=[C:22]([O:30][CH3:31])[CH:21]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 53696622HCID 53696622, compound

Product 1

HCID 53866133HCID 53866133, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-(3-tert-Butoxycarbonylaminomethylpyrrolidin-1-yl)propylamine (5 g) was dissolved in dimethylformamide (50 ml) and 4-amino-5-chloro-2-methoxybenzoic acid (3.9 g) and 1-hydroxybenzotriazole (3.2 g) were added. The mixture was stirred at 0° C. for 15 min and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (4.5 g) was added, followed by stirring at room temperature for 10 hr. The reaction mixture was concentrated under reduced pressure, and aqueous potassium carbonate solution was added to the residue. The mixture was extracted with ethyl acetate, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 3.4 g of 4-amino-N-(3-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)propyl)-5-chloro-2-methoxybenzamide.

Workup

  1. stirringby stirring at room temperature for 10 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and aqueous potassium carbonate solution
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d5d704828778425088bd64640ff631af
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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