Sodium Iodide → N-{[5-(6-Bromo-1H-indazol-4-yl)-1,3,4-oxadiazol-2-yl]methyl}-3-(4-morpholinyl)-1-propanamine

HRID 38845

Reaktionsgleichung

Reaktionsgleichung von HRID 38845
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2S(C2C=CC=CC=2)(=O)=O)=[C:4]([C:20]2[O:21][C:22]([CH2:25]Cl)=[N:23][N:24]=2)[CH:3]=1.[I-].[Na+].[N:29]1([CH2:35][CH2:36][CH2:37][NH2:38])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>C(#N)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([C:20]2[O:21][C:22]([CH2:25][NH:38][CH2:37][CH2:36][CH2:35][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[N:23][N:24]=2)[CH:3]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 666956686-bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole

Produkt 1

HCID 66693558N-{[5-(6-Bromo-1H-indazol-4-yl)-1,3,4-oxadiazol-2-yl]methyl}-3-(4-morpholinyl)-1-propanamineAusbeute 117,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole (300 mg, 0.661 mmol) and sodium iodide (99 mg, 0.661 mmol) were weighed into a round-bottomed flask and dissolved in acetonitrile (2 ml) before [3-(4-morpholinyl)propyl]amine (191 mg, 1.322 mmol, available from Sigma-Aldrich) and DIPEA (0.231 ml, 1.322 mmol) were added. The mixture was heated to 70° C. for 2 h, then cooled and the solvent removed under a stream of nitrogen. The crude residue was dissolved in DCM/MeOH (1:1) and preadsorbed onto silica which was then added to the top of a 20 g silica cartridge that was subsequently eluted with 0-15% MeOH(+1% triethylamine)/DCM over 20 mins. The appropriate fractions were combined and the solvent removed in vacuo to give the title compound as a yellow oily solid (328 mg).

Aufarbeitung

  1. additionwere added
  2. temperaturecooled
  3. customthe solvent removed under a stream of nitrogen
  4. dissolutionThe crude residue was dissolved in DCM/MeOH (1:1)
  5. additionwas then added to the top of a 20 g silica cartridge that
  6. washwas subsequently eluted with 0-15% MeOH(+1% triethylamine)/DCM over 20 mins
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-efdc4be0799741cea96b3527d01e17f1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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