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Triethylamine → HCID 21993898, Verbindung

HRID 1978519
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1978519
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:38][CH2:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([C:48](=[O:55])[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43]1.C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C>C(#N)C>[C:48]([N:45]1[CH2:44][CH2:43][N:42]([CH2:41][CH2:40][CH2:39][NH:38][C:13]([C:5]2[S:6][C:7]3[N:12]4[C:3](=[CH:2][N:1]=[C:11]4[CH:10]=[CH:9][CH:8]=3)[CH:4]=2)=[O:15])[CH2:47][CH2:46]1)(=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, VerbindungHCID 21993726HCID 21993726, Verbindung

Produkt 1

HCID 21993898HCID 21993898, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.8 g (3.67 mmol.) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.84 g (8.8 mmol.) of N-hydroxysuccinimide in acetonitrile (15 ml) was added, at room temperature, 1.41 g (7.36 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride. The mixture was stirred for 2 hours. To the reaction system was added a solution of 1.41 g (4.4 mmol.) of 4-(3-aminopropan-1-yl)-1-benzoylpiperazin dihydrochloride, 1.34 g (8.8 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 1.0 ml (7.17 mmol.) of triethylamine in acetonitrile (15 ml). The mixture was stirred for further 2 hours. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate (a small volume of ethanol was also used). The organic layer was washed with a saturated aqueous saline solution, dried over magnesium sulfate and subjected to to distillation under reduced pressure. The residue was subjected to fractional purification by means of a column chromatography (methanol/ethyl acetate 30-40%), followed by distilling off the solvent under reduced pressure to afford the object compound as a reddish purple crystalline product. The yield was 0.738 g (45%).

Aufarbeitung

  1. additionwas added, at room temperature
  2. stirringThe mixture was stirred for further 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water, which
  5. extractionwas subjected to extraction with ethyl acetate (a small volume of ethanol
  6. washThe organic layer was washed with a saturated aqueous saline solution
  7. dry with materialdried over magnesium sulfate
  8. distillationsubjected to to distillation under reduced pressure
  9. customThe residue was subjected to fractional purification by means of a column chromatography (methanol/ethyl acetate 30-40%)
  10. distillationby distilling off the solvent under reduced pressure
  11. customto afford the object compound as a reddish purple crystalline product

Quellen und Nachweise

ORD-Eintrag
ord-ae9ec412db0a452cad3db50667b9faee
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06235731B1

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