Sodium Iodide → 6-Bromo-4-(5-{[(3R,5S)-3,5-dimethyl-4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

HRID 520538ノート

反応式

HRID 520538 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([CH2:25]Br)=[N:23][N:24]=2)[CH:3]=1.[CH3:27][C@@H:28]1[CH2:33][NH:32][CH2:31][C@H:30]([CH3:34])[N:29]1[CH:35]([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.[I-].[Na+]>C(#N)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[C:4]([C:20]2[O:21][C:22]([CH2:25][N:32]3[CH2:31][C@H:30]([CH3:34])[N:29]([CH:35]([CH3:37])[CH3:36])[C@H:28]([CH3:27])[CH2:33]3)=[N:23][N:24]=2)[CH:3]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 10583032(2R,6S)-2,6-Dimethyl-1-(1-methylethyl)piperazineHCID 667769666-Bromo-4-[5-(bromomethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole

生成物 1

HCID 667785236-Bromo-4-(5-{[(3R,5S)-3,5-dimethyl-4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

6-Bromo-4-[5-(bromomethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole (200 mg, 0.441 mmol) in acetonitrile (2 ml) was treated with (2R,6S)-2,6-dimethyl-1-(1-methylethyl)piperazine (138 mg, 0.883 mmol, see J. Med. Chem., 1999, 42, 1123-1144 for literature preparation), DIPEA (0.154 ml, 0.8825 mmol) and sodium iodide (66 mg, 0.44 mmol). The reaction mixture was heated at 70° C. for 5 h. The reaction mixture was then cooled, diluted with DCM and washed with an aqueous 2M HCl solution (5 ml). The organic layer was separated using a hydrophobic frit, washed with water and the solvent removed under a stream of nitrogen to give the title compound as a brown oil.

後処理

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with an aqueous 2M HCl solution (5 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. customthe solvent removed under a stream of nitrogen

出典と根拠

ORDレコード
ord-7c99a30ae6604787b0a1d09b9ec70fb7
出典データセット
uspto-grants-2016_05
特許番号
US09326987B2

反応ノート

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