Hydrochloric Acid → 6-(1H-Indol-4-yl)-4-{5-[(phenylsulfonyl)methyl]-1,3,4-oxadiazol-2-yl}-1H-indazole

HRID 38878

Reaktionsgleichung

Reaktionsgleichung von HRID 38878
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:16]=[C:15]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][N:12]3S(C2C=CC=CC=2)(=O)=O)=[N:5][N:4]=1.O.O.[C:37]1([S:43]([O-:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Na+].[OH-].[Na+].Cl>C(O)C.C(O)(C)C.CO.ClCCl>[NH:21]1[C:22]2[C:18](=[C:17]([C:15]3[CH:14]=[C:13]4[C:9]([CH:10]=[N:11][NH:12]4)=[C:8]([C:6]4[O:7][C:3]([CH2:2][S:43]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)(=[O:45])=[O:44])=[N:4][N:5]=4)[CH:16]=3)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23681562Benzenesulfinic acid, sodium salt, dihydrateHCID 667769544-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole

Produkt 1

HCID 667769046-(1H-Indol-4-yl)-4-{5-[(phenylsulfonyl)methyl]-1,3,4-oxadiazol-2-yl}-1H-indazoleAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (60 mg, 0.110 mmol) and sodium benzenesulfinate dihydrate (33.1 mg, 0.165 mmol, available from TCI Europe) in ethanol (0.8 ml) were heated under microwave irradiation to 100° C. for 30 mins then 150° C. for 20 mins. The mixture was treated with dichloromethane (3 ml) and methanol (3 ml) and absorbed onto Florisil. This was placed on top a silica cartridge (10 g) and eluted with 0-100% ethyl acetate/cyclohexane and then 0-20% methanol/ethyl acetate. Appropriate fractions were combined and concentrated to give a yellow solid, 33 mg. The solid was treated with isopropanol (1 ml) and 2M aqueous sodium hydroxide (0.999 ml, 1.998 mmol) and stirred at 20° C. for 22 h. The mixture was neutralised with 2M aqueous hydrochloric acid, blown to dryness and purified by Mass Directed Automated Preparative HPLC. Appropriate fraction was evaporated, then azeotroped with methanol to give the title compound as a white solid (8 mg).

Aufarbeitung

  1. customabsorbed onto Florisil
  2. washeluted with 0-100% ethyl acetate/cyclohexane
  3. concentrationconcentrated
  4. customto give a yellow solid, 33 mg
  5. custompurified by Mass Directed Automated Preparative HPLC
  6. customAppropriate fraction was evaporated
  7. customazeotroped with methanol

Quellen und Nachweise

ORD-Eintrag
ord-20985be666024876a39c0789702ab1c5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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