Tetrahydrofuran → HCID 69655662, Verbindung

HRID 11566

Reaktionsgleichung

Reaktionsgleichung von HRID 11566
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C1COCC1>[Pd].CO>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([CH2:23][NH2:24])=[CH:21][CH:22]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 69655660{2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Produkt 1

HCID 69655662HCID 69655662, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In a flask, 2920 mg (8.72 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester and 1000 mg Pd (10% on carbon) were placed under nitrogen and 10 ml THF and 120 ml methanol were added. The starting material was hydrogenated under atmospheric pressure and at rt for 3.5 h. The catalyst was filtered off. The solvent was evaporated and the residue was subjected to silica gel chromatography (toluene/isopropanol/NH3 (conc.) 16:20:1) to yield 2600 mg (7.6 mmol) {2-[(6-Aminomethyl-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; exact MW [M+H] calc'd: 343.18; MW found [M+H]: 343.2.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5d0d19c1f38d4ac39a2931cfcb53fdfb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098247B2

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