Pyridine → {2-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenyl}-(methylsulfonyl)amine

HRID 228129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228129
[CH2:1]([CH:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][CH:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:22][S:23](NC1C=CC=CC=1N1CCN(C(OC(C)(C)C)=O)CC1)(=[O:25])=[O:24].CS(Cl)(=O)=O.N1C=CC=CC=1>>[CH2:1]([CH:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][CH:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][S:23]([CH3:22])(=[O:25])=[O:24])[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-PiperazinecarboxylateHCID 219352252-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]-phenylamine

Produkt 1

HCID 21935158{2-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenyl}-(methylsulfonyl)amine

Versuchsvorschrift

{2-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenyl}-(methylsulfonyl)amine was prepared from 2-[2,5-diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenylamine (Step 2) (690 mg, 2.5 mmol) according to the procedure for Preparation III using methanesulfonyl chloride (190 μl, 2.46 mmol) and pyridine (220 μl, 2.72 mmol). The crude mix was purified by flash chromatography (SiO2, 3% MeOH in CH2Cl2) to afford the desired sulfonamide (533 mg). MS (ESI, pos. ion) m/z: 358 (M+H), (ESI, neg. ion) m/z: 356 (M−H). Calc'd for C19H23N3O2S: 357.47.

Aufarbeitung

  1. additionThe crude mix
  2. customwas purified by flash chromatography (SiO2, 3% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-99a5ba3d0c0a44ba99fdc39459a033cf
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560460B2

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