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Ethanol → HCID 23130529, Verbindung

HRID 2079969
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2079969
[NH2:1][C:2]1[N:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:2]1[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 231304292-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Produkt 1

HCID 23130529HCID 23130529, VerbindungAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (74 mg, 0.20 mmol) described in Preparation Example A+-9, an iron powder (56 mg, 1.0 mmol) and ammonium chloride (21 mg, 0.40 mmol) were suspended in a solvent mixture of ethanol (2 mL) and water (0.5 mL), the solution was stirred at 60° C. for 3 hours, then, it was stirred at 90° C. for 6 hours. The reaction solution was cooled to room temperature, then, it was filtered through Celite pad. The filtrate was evaporated in vacuo, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water:mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (54.4 mg) was obtained as a trifluoroacetic acid salt.

Aufarbeitung

  1. stirringit was stirred at 90° C. for 6 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationit was filtered through Celite pad
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water:mobile phase (containing 0.1% trifluoroacetic acid) was used)

Quellen und Nachweise

ORD-Eintrag
ord-c688d761f13644d4bce8b0ae6496e5ee
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932272B2

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