p-Cyanobenzenesulphonamide → 4-(5-{4-(2-Methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide

HRID 219918

反応式

HRID 219918 の反応式
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:13][OH:14])[NH2:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(C1C=CC(S(N)(=O)=O)=CC=1)#N.[CH3:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=O)=[CH:36][C:35]=1[NH:43][S:44]([CH3:47])(=[O:46])=[O:45]>>[CH3:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[C:34]1[CH:42]=[CH:41][C:37]([C:38]2[O:14][N:13]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[N:12]=2)=[CH:36][C:35]=1[NH:43][S:44]([CH3:47])(=[O:45])=[O:46]

参加物

4

反応物 3

HCID 76566p-CyanobenzenesulphonamideHCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 584433444-(2-Methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]benzoic acid

生成物 1

HCID 252563834-(5-{4-(2-Methylpiperidin-1-yl)-3-[(methylsulfonyl)amino]phenyl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-93765c885bc94c4c998c1bde5243cd54
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

読み込み中…