1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone → HCID 178465622, Verbindung

HRID 1821868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821868
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=O)[CH3:11].[C:13]([NH:16][NH2:17])([NH2:15])=[NH:14].[ClH:18]>C(O)C.Cl>[ClH:18].[ClH:18].[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[N:17][NH:16][C:13]([NH2:15])=[NH:14])[CH3:11]

Komponenten

5

Edukt 2

HCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanoneHCID 178418668HCID 178418668, Verbindung

Produkt 1

HCID 178465622HCID 178465622, VerbindungAusbeute 161,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone (Example 70) (90 mg, 0.56 mmol) and aminoguanidine hydrochloride (65 mg, 0.59 mmol) in ethanol (5.6 mL) and 6 N HCl (0.47 mL) was heated under reflux for 1.5 h. The reaction mixture was cooled to room temperature and the precipitate was filtered, rinsed with ethanol and diethyl ether, and dried under vacuum at 45° C. to provide [[1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylidene]amino]guanidine dihydrochloride (138 mg, 86%) as a white solid: mp 314-318° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.50 (3H, s), 7.40 (1H, s), 8.10-8.27 (2H, m), 9.04 (1H, s); ESI MS m/z 217 [C10H12N6+H]+; HPLC (Method A) >99% (AUC), tR=9.01 min.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. filtrationthe precipitate was filtered
  4. washrinsed with ethanol and diethyl ether
  5. customdried under vacuum at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-ea8ba445279a461ca1eab23e704a9187
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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