Reaktion #307100

Reaktionsgleichung

Intermediate 25

4-(2-methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]benzoic acid

4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide

4-cyanobenzene-1-sulfonamide

→

title compound

4-(5-{4-(2-methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title compound was prepared following procedure
2. 2
   Sonstigeprepared
3. 3
   SonstigeThe reaction mixture was evaporated
4. 4
   Sonstigewas purified by flash chromatography (c-hex/EtOAc: 9.5/0.5)

Vorschrift

The title compound was prepared following procedure described for example 4, step 1, but starting from 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide, prepared as described in WO 2006/013104 A1 from 4-cyanobenzene-1-sulfonamide (ABCR; CD10716), (322.85 mg; 1.50 mmol) and Intermediate 25 (562.30 mg; 1.80 mmol). The reaction mixture was evaporated under reduce pressure and was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound as a pale yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.68 (br s, 1H), 8.31-8.27 (m, 2H), 8.22 (d, J=2.0 Hz, 1H), 8.06-8.03 (m, 2H), 7.94 (dd, J=8.2, 1.8 Hz, 1H), 7.57 (br s, 2H), 7.55 (s, 1H), 3.23 (s, 3H), 3.20-3.13 (m, 1H), 2.94-2.87 (m, 1H), 2.66-2.57 (m, 1H), 1.84-1.66 (m, 4H), 1.50-1.44 (m, 2H), 0.82 (d, J=6.1 Hz, 3H). LC/MS (Method B): 490.4 (M−H)−, 492.4 (M+H)+. HPLC (Method A) Rt 4.34 min (Purity: 97.9%).

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