1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl [1-[3-[(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetylamino]propyl]piperidin-4-yl]carboxylate

HRID 1059372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059372
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][C:16]([OH:18])=O)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O.C(N(CC)CC)C.CN(C)C=O>[CH2:34]([O:33][C:31]([CH:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH2:22][NH:21][C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:7]3[S:6][C:5]4[N:4]=[CH:3][CH:2]=[N:1][C:10]=4[NH:9][C:8]=3[CH:11]=2)[CH2:30][CH2:29]1)=[O:32])[CH3:35]

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1867013310H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetic acidHCID 18670238Ethyl 1-(3-aminopropyl)piperidine-4-carboxylate dihydrochloride

Produkt 1

HCID 23564778Ethyl [1-[3-[(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetylamino]propyl]piperidin-4-yl]carboxylateAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 10 ml of N,N-dimethylformamide were added 0.6 g of 10H-pyrazino[2,3-b][1,4]benzothiazine-8-acetic acid, 0.8 g of ethyl 1-(3-aminopropyl)piperidine-4-carboxylate dihydrochloride, 0.38 g of 1-hydroxybenzotriazole, 1.07 ml of triethylamine and 0.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and the resulting mixture was stirred at room temperature for 22 hours. After adding water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium. chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol). The crystals thus obtained were washed with ether and thus 0.72 g of the title compound was obtained as a pale brown powder.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialchloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)
  6. customThe crystals thus obtained
  7. washwere washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-72d513cf955548f5b6168260afd30beb
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518423B1

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