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 520612

반응식

HRID 520612 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ad3361f4e513427aa092b1e6b6cefb5b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326987B2

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