Methanol → HCID 59603016, Verbindung

HRID 1951416

Reaktionsgleichung

Reaktionsgleichung von HRID 1951416
[C:1]([C:4]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[C:23]([F:26])([F:25])[F:24])[C:12]2[C:11](=[O:27])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:28])(=[O:3])[CH3:2].FC(F)(F)S(O[CH2:35][CH3:36])(=O)=O.CO>C1COCC1>[CH2:35]([O:27][C:11]1[N:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24])[C:4]([C:1](=[O:3])[CH3:2])=[C:5]([CH3:28])[NH:6]2)[CH3:36]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 67924Ethyl trifluoromethanesulphonateHCID 596030333-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Produkt 1

HCID 59603016HCID 59603016, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

976 mg (2.48 mmol) of 3-acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one are suspended in THF (60 ml), and 3 ml (3 mmol) of N′″-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane) are added. Then 389 μl (2.97 mmol) of ethyl trifluoromethanesulfonate are added to the dark red solution. The decolorized solution is stirred for a further 10 min and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 240 mg (23% of theory) of the title compound as a white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4082b395f898481ba6da9e66567640fc
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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