Dimethylformamide → 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile
Reaktionsgleichung
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)(=[O:17])=[O:16].[CH3:23][N:24](C=O)C>C(#N)C>[CH3:7][C:5]1[NH:4][C:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:2]([CH3:1])[C:6]=1[C:23]#[N:24]Komponenten
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A mixture of 3,5-dimethyl-2-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (576.0 mg, 1.809 mmol) and N-chlorosulfonylisocyanide (197 μl, 2.261 mmol) in acetonitrile (9.0 ml) was stirred at 25° C. for 1 hour. DMF (140 μl, 1.809 mmol) was then added and the resulting mixture was stirred for an additional 16 hours. It was quenched with water (100 ml) and extracted with dichloromethane (100 ml×2). The organic layers were combined, filtered, and evaporated to give an oil. The oil was purified by column chromatography (0 to 70% ethyl acetate in hexanes) to give 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile (513.6 mg, 1.495 mmol, 83% yield) as brown oil. 1H NMR (CDCl3/400 MHz) δ (ppm) 9.10 (bs, 1H), 7.82-7.77 (m, 1H), 7.46-7.40 (m, 1H), 7.30-7.23 (m, 2H), 4.10 (s, 2H), 3.33-3.27 (m, 4H), 2.20 (s, 3H), 2.18 (s, 3H), 1.92-1.88 (m, 4H). MS m/z: 344.3 (M+1).
Aufarbeitung
- stirringthe resulting mixture was stirred for an additional 16 hours
- customIt was quenched with water (100 ml)
- extractionextracted with dichloromethane (100 ml×2)
- filtrationfiltered
- customevaporated
- customto give an oil
- customThe oil was purified by column chromatography (0 to 70% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-e3ec5a4e907d4f1b830f23656e540c3c
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08674115B2
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