Acetone → HCID 54575147, Verbindung

HRID 2190157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190157
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:25][C:11]3=[N:12][C:13]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[C:14](C(C)=C)[CH:15]=[C:10]3[C:9]=2[C:26]([NH:28][CH3:29])=[O:27])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:34]CC1.[CH3:38][C:39]([CH3:41])=[O:40]>>[OH:34][CH2:38][C:39]([C:14]1[CH:15]=[C:10]2[C:9]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[O:25][C:11]2=[N:12][C:13]=1[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])([OH:40])[CH3:41]

Komponenten

4

Edukt 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 54576013HCID 54576013, Verbindung

Produkt 1

HCID 54575147HCID 54575147, Verbindung

Versuchsvorschrift

To 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (11 mg, 0.026 mmol) in acetone (1 ml) was added NMO (9.26 mg, 0.079 mmol) and potassium osmate dihydrate (0.971 mg, 2.64 μmol). After LCMS indicated predominant conversion of starting material to product, the reaction mixture was purified by HPLC to afford the title compound. MS (ESI) m/z 452.0 (M+1). 2 rotamers confirmed by 2D NMR: 1H NMR (400 MHz, CD3CN) δ ppm 8.66, 8.64 (s, 1H), 8.04-8.02 (m, 2H), 7.34-7.29 (m, 2H), 6.88 (br s, 1H), 4.16-4.13, 4.06-4.03 (m, 1H), 3.92, 3.88 (br s, 1H), 3.82-3.79 (m, 1H), 3.33, 3.32 (s, 3H), 3.29 (s, 3H), 3.15-3.02 (br s, 1H), 2.93-2.92 (d, 3H)

Aufarbeitung

  1. customthe reaction mixture was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-79b7a1e65273454498135b82beb8fe2c
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324239B2

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