4-Benzoylpiperidine hydrochloride → 5-[5-(4-Benzoylpiperidine-1-sulfonyl)thiophen-2-yl]-3-ethyl-6-methyl-1H-pyridin-2-one

HRID 1921444

Reaktionsgleichung

Reaktionsgleichung von HRID 1921444
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].Cl.[C:21]1([C:27]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:27]([CH:29]1[CH2:34][CH2:33][N:32]([S:16]([C:14]2[S:15][C:11]([C:5]3[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=3[CH3:10])=[CH:12][CH:13]=2)(=[O:18])=[O:17])[CH2:31][CH2:30]1)(=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

3

Edukt 2

HCID 27244374-Benzoylpiperidine hydrochlorideHCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

Produkt 1

HCID 588085995-[5-(4-Benzoylpiperidine-1-sulfonyl)thiophen-2-yl]-3-ethyl-6-methyl-1H-pyridin-2-oneAusbeute 85 %

Versuchsvorschrift

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with phenyl-piperidin-4-yl-methanone hydrochloride as described in Step 5, Example 24 to give the title compound as a yellow solid (85% yield). LC/MS: RT 3.27 min, m/e 471 (M+H); 1H NMR (CDCl3, δ, ppm): 11.95 (1H, s), 7.89 (2H, dd), 7.55-7.60 (1H, m), 7.44-7.52 (3H, m), 7.33 (1H, s), 7.01 (1H, d), 3.79-3.84 (2H, m), 3.27-3.36 (1H, m), 2.73-2.82 (2H, m), 2.60 (2H, q), 2.48 (3H, s), 1.89-2.05 (4H, m), 1.24 (3H, t).

Quellen und Nachweise

ORD-Eintrag
ord-5d83e873278542a6882c7abaf8a3b2c4
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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