1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131722620, compound

HRID 1066570Notes

Reaction equation

HRID 1066570 reaction equation
C([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:9]1=[O:19])(C)(C)C.[CH3:21][O:22][C:23]1[CH:48]=[CH:47][C:26]([CH2:27][CH:28]([CH2:32][C:33](=[O:46])[N:34]2[CH2:39][CH2:38][N:37]([C:40]3[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=3)[CH2:36][CH2:35]2)[C:29](O)=[O:30])=[CH:25][CH:24]=1.Cl.C(N=C=NCCCN(C)C)C>C(#N)C>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][C@@H:28]([CH2:32][C:33](=[O:46])[N:34]2[CH2:35][CH2:36][N:37]([C:40]3[CH:41]=[CH:42][N:43]=[CH:44][CH:45]=3)[CH2:38][CH2:39]2)[C:29]([N:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:5])=[O:20])[C:9](=[O:19])[CH:10]2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:30])=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10636945HCID 10636945, compoundHCID 21200233HCID 21200233, compound

Product 1

HCID 131722620HCID 131722620, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (S)-(3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid tert-butyl ester (0.29 g) and 2-(4-methoxybenzyl)-4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)butanoic acid (0.385 g) produced in Reference Example 9 in acetonitrile (30 ml) was added 1-ethyl-3-(3-di-methylaminopropyl)carbodiimide hydrochloride (0.4 g) and the suspension was stirred for 24 hours at room temperature. The reaction mixture was concentrated under reduced pressure and purified by means of a silica gel column chromatography (acetonitrile:methanol=7:3). To the produced ester derivative was added trifluoroacetic acid (6 ml) and the solution was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by means of CHP-20 column chromatography (H2O→20% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound (0.35 g) as a white amorphous powdery product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by means of a silica gel column chromatography (acetonitrile:methanol=7:3)
  3. additionTo the produced ester derivative was added trifluoroacetic acid (6 ml)
  4. stirringthe solution was stirred for 2 hours at room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe concentrate was purified by means of CHP-20 column chromatography (H2O→20% acetonitrile aqueous solution)
  7. concentrationThe objected fraction was concentrated

Sources & evidence

ORD record
ord-900e1990ba2c4adc95deca4e1f2a1850
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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