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 520538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520538
[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

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7c99a30ae6604787b0a1d09b9ec70fb7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326987B2

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