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

Reaktionsgleichung

Reaktionsgleichung von HRID 38863
[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

Komponenten

8

Edukt 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

Produkt 1

HCID 667767816-(1H-Indol-4-yl)-4-[5-({4-[2-(4-morpholinyl)ethyl]-1-piperazinyl}methyl)-1,3,4-oxadiazol-2-yl]-1H-indazoleAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a395d4ab713344a8a1db6a2018ac61b2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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