Lawesson's reagent → 5-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-thioxo-morpholin-3-yl)-pyridin-2-yl]-amide

HRID 474051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474051
[F:1][CH2:2][C:3]1([C:10]2[N:15]=[C:14]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][CH2:6][C:5](=O)[NH:4]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1COCC1>[F:1][CH2:2][C:3]1([C:10]2[N:15]=[C:14]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][CH2:6][C:5](=[S:35])[NH:4]1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 866680245-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-oxo-morpholin-3-yl)-pyridin-2-yl]-amide

Produkt 1

HCID 866680255-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-thioxo-morpholin-3-yl)-pyridin-2-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-oxo-morpholin-3-yl)-pyridin-2-yl]-amide (0.24 g, 0.658 mmol) in THF (10.0 ml), Lawesson's reagent (0.798 g, 1.974 mmol) was added at rt and heated at reflux temperature for 24 h. Reaction mass was concentrated under reduced pressure. The crude compound was directly purified by column chromatography using 23% ethyl acetate in hexane to furnish title compound as off-white solid. Yield=0.19 g (72% [2 steps]). TLC (50% ethyl acetate in hexane) Rf=0.71; LCMS: RtH8=1.578, [M+1]+=381.1 and 382.9.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for 24 h
  3. customReaction mass
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude compound was directly purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-66b2c848d6df4881aa063bee81ceba43
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637508B2

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