Sodium Iodide → 4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-6-(1H-indol-4-yl)-1H-indazole

HRID 38862

Reaktionsgleichung

Reaktionsgleichung von HRID 38862
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.Cl[CH2:10][C:11]1[O:15][C:14]([C:16]2[CH:24]=[C:23]([C:25]3[CH:33]=[CH:32][CH:31]=[C:30]4[C:26]=3[CH:27]=[CH:28][NH:29]4)[CH:22]=[C:21]3[C:17]=2[CH:18]=[N:19][N:20]3S(C2C=CC=CC=2)(=O)=O)=[N:13][N:12]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+].[OH-].[Na+]>C(#N)C.C(O)(C)C>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([CH2:10][C:11]2[O:15][C:14]([C:16]3[CH:24]=[C:23]([C:25]4[CH:33]=[CH:32][CH:31]=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)[CH:22]=[C:21]4[C:17]=3[CH:18]=[N:19][NH:20]4)=[N:13][N:12]=2)[CH2:5]1

Komponenten

8

Edukt 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 6415002,6-Dimethylmorpholine, cis-HCID 667769544-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole

Produkt 1

HCID 667768284-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-6-(1H-indol-4-yl)-1H-indazoleAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(2R,6S)-2,6-Dimethylmorpholine (12.57 mg, 0.11 mmol) and 4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (51 mg, 0.104 mmol) were dissolved in acetonitrile (0.5 ml) and N,N-diisopropylethylamine (0.0262 ml, 0.15 mmol) was added, followed by sodium iodide (14.99 mg, 0.1 mmol). The solution was stirred at 70° C. for 18 h and blown to dryness under a stream of nitrogen. Isopropanol (0.5 ml) was added followed by 2M sodium hydroxide (0.5 ml) and stirred for 18 h when the mixture was neutralised and the solvent removed under a stream of nitrogen. The crude product was dissolved in dimethylsulphoxide (0.5 ml) and purified by Mass Directed Automated Preparative HPLC (Method F) and the solvent was evaporated in vacuo using Genevac to give the title compound (4 mg).

Aufarbeitung

  1. stirringstirred for 18 h when the mixture
  2. customthe solvent removed under a stream of nitrogen
  3. dissolutionThe crude product was dissolved in dimethylsulphoxide (0.5 ml)
  4. custompurified by Mass Directed Automated Preparative HPLC (Method F)
  5. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c756c05db4ff44339989f36d54ca88a2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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