1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Propyl 3-{[2-(Acetylamino)ethylthio]methyl}-4-oxo-4-(3-pyridyl)butanoate

HRID 2184740

Reaction equation

HRID 2184740 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][CH2:8][CH:9]([C:14](=[O:21])[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].Cl.CN(C)[CH2:25][CH2:26][CH2:27]N=C=NCC>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([NH:4][CH2:5][CH2:6][S:7][CH2:8][CH:9]([C:14](=[O:21])[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][C:11]([O:13][CH2:25][CH2:26][CH3:27])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99445253-{[2-(Acetylamino)ethylthio]methyl}-4-oxo-4-(3-pyridyl)butanoic acid

Product 1

HCID 22457756Propyl 3-{[2-(Acetylamino)ethylthio]methyl}-4-oxo-4-(3-pyridyl)butanoateYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-{[2-(acetylamino)ethylthio]methyl}-4-oxo-4-(3-pyridyl)butanoic acid (0.1 g), 1[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (68.1 mg) and 4-dimethylaminopyridine (0.1 eq) in dimethyl formamide (2 mL) was stirred for 24 h. The solution was purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 0.085 g (75%) of the title compound; ESMS (M+1)+353.

Workup

  1. customThe solution was purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA)

Sources & evidence

ORD record
ord-00b538251eb4485ab9ca724be8437ff2
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Linked notes

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