Dimethylformamide → HCID 70232414, compound

HRID 1066569Notes

Reaction equation

HRID 1066569 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[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:30][CH2:29]1)[CH2:23][CH2:24][C:25](O)=[O:26].CN(C)C=O.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[CH2:29][CH2:30][N:31]([C:34]3[N:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH2:32][CH2:33]2)[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:5])=[O:20])[C:9]1=[O:19])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2815239213186-60-8HCID 10636945HCID 10636945, compound

Product 1

HCID 70232414HCID 70232414, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (S)-(3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid tert-butyl ester (0.45 g) and 4-oxo-4-(4-pyrimidin-2-ylpiperazin-1-yl)butanoic acid (0.46 g) produced in Reference Example 4 in acetonitrile (20 ml) and dimethylformamide (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.36 g) and the suspension was stirred for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure. To the solution was added saturated brine and the solution was extracted with ethyl acetate. The extract was dried over Na2SO4 and was concentrated under reduced pressure. To the produced ester derivative was added trifluoroacetic acid (10 ml) and the mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound (0.45 g) as a white amorphous powdery product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the solution was added saturated brine
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationwas concentrated under reduced pressure
  6. additionTo the produced ester derivative was added trifluoroacetic acid (10 ml)
  7. stirringthe mixture was stirred for 2 hours at room temperature
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe concentrate was purified by CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution)
  10. concentrationThe objected fraction was concentrated

Sources & evidence

ORD record
ord-bb0d11653ee3442c94703d0164949903
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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