Sodium Iodide → 6-(1H-Indol-4-yl)-4-[5-({4-[2-(4-morpholinyl)ethyl]-1-piperazinyl}methyl)-1,3,4-oxadiazol-2-yl]-1H-indazole

HRID 38863

反応式

HRID 38863 の反応式
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:16][C:17]1[O:21][C:20]([C:22]2[CH:30]=[C:29]([C:31]3[CH:39]=[CH:38][CH:37]=[C:36]4[C:32]=3[CH:33]=[CH:34][NH:35]4)[CH:28]=[C:27]3[C:23]=2[CH:24]=[N:25][N:26]3S(C2C=CC=CC=2)(=O)=O)=[N:19][N:18]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+].[OH-].[Na+]>C(#N)C.C(O)(C)C>[NH:35]1[C:36]2[C:32](=[C:31]([C:29]3[CH:28]=[C:27]4[C:23]([CH:24]=[N:25][NH:26]4)=[C:22]([C:20]4[O:21][C:17]([CH2:16][N:4]5[CH2:3][CH2:2][N:1]([CH2:7][CH2:8][N:9]6[CH2:10][CH2:11][O:12][CH2:13][CH2:14]6)[CH2:6][CH2:5]5)=[N:18][N:19]=4)[CH:30]=3)[CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:34]1

参加物

8

反応物 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27346404-(2-Piperazin-1-yl-ethyl)-morpholineHCID 667769544-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole

生成物 1

HCID 667767816-(1H-Indol-4-yl)-4-[5-({4-[2-(4-morpholinyl)ethyl]-1-piperazinyl}methyl)-1,3,4-oxadiazol-2-yl]-1H-indazole収率 50.5%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

4-[2-(1-piperazinyl)ethyl]morpholine (14.1 mg, 0.11 mmol) and 4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (50 mg, 0.102 mmol) were dissolved in acetonitrile (0.5 ml) and N,N-diisopropylethylamine (0.026 ml, 0.15 mmol) was added, followed by sodium iodide (15.3 mg, 0.102 mmol). The solution was stirred at 70° C. for 18 h and blown to dryness under a stream of nitrogen. Isopropanol (0.3 ml) was added followed by 2M sodium hydroxide (0.3 ml) and stirred for 5 h when the mixture was neutralised and the solvent removed under a stream of nitrogen. The crude product was dissolved in dimethylsulphoxide (0.3 ml) and methanol (0.15 ml) with formic acid (0.05 ml) then purified by Mass Directed Automated Preparative HPLC (Method F) to give the title compound (26.4 mg).

後処理

  1. stirringstirred for 5 h when the mixture
  2. customthe solvent removed under a stream of nitrogen
  3. dissolutionThe crude product was dissolved in dimethylsulphoxide (0.3 ml)
  4. custommethanol (0.15 ml) with formic acid (0.05 ml) then purified by Mass Directed Automated Preparative HPLC (Method F)

出典と根拠

ORDレコード
ord-a395d4ab713344a8a1db6a2018ac61b2
出典データセット
uspto-grants-2013_09
特許番号
US08524751B2

関連ノート

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