4-oxo-4-[4-(pyridin-2-yl)piperazin-1-yl]butanoic acid → HCID 54493751, compound

HRID 1066568Notes

Reaction equation

HRID 1066568 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.[O:21]=[C:22]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:30][CH2:29]1)[CH2:23][CH2:24][C:25](O)=[O:26].Cl.C(N=C=NCCCN(C)C)C>C(#N)C>[CH3:18][O:17][C:15]([CH2:14][C@@H:10]1[N:11]([C:25](=[O:26])[CH2:24][CH2:23][C:22](=[O:21])[N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH2:30][CH2:29]2)[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:5])=[O:20])[C:9]1=[O:19])=[O:16]

Participants

5

Reactant 3

HCID 7357834-oxo-4-[4-(pyridin-2-yl)piperazin-1-yl]butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10636945HCID 10636945, compound

Product 1

HCID 54493751HCID 54493751, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To suspension of (S)-(3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid tert-butyl ester (0.64 g) and 4-oxo-4-(4-pyridin-2-ylpiperazin-1-yl)butanoic acid (0.65 g) produced in Reference Example 3 in acetonitrile (20 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.52 g) and the suspension was stirred for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by means of a silica gel column chromatography (acetonitrile/methanol=9/1). To the produced ester derivative was added trifluoroacetic acid (10 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→10% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound (0.84 g) as a white amorphous powdery product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe concentrate was purified by means of a silica gel column chromatography (acetonitrile/methanol=9/1)
  3. additionTo the produced ester derivative was added trifluoroacetic acid (10 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→10% acetonitrile aqueous solution)
  7. concentrationThe objected fraction was concentrated

Sources & evidence

ORD record
ord-0b2a2c1d82dc4362b4af706192b95813
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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