Potassium Carbonate → 9-(benzo[d]oxazol-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one

HRID 41565

Reaktionsgleichung

Reaktionsgleichung von HRID 41565
[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][N:21]3[C:26]4([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH2:25][CH2:24][CH2:23][C:22]3=[O:32])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[C:40]1[O:41][C:42]2[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=2[N:44]=1>CN(C=O)C>[O:41]1[C:42]2[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=2[N:44]=[C:40]1[N:29]1[CH2:30][CH2:31][C:26]2([N:21]([CH2:20][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[CH:13]=[CH:12][N:11]4[S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:2])=[O:3])[C:22](=[O:32])[CH2:23][CH2:24][CH2:25]2)[CH2:27][CH2:28]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 672515941-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one

Produkt 1

HCID 672523209-(benzo[d]oxazol-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the stirred solution of 1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one (TFA salt) (300 mg, 0.55 mmol) in DMF (6 mL) were added K2CO3 (380 mg, 2.75 mmol) and 2-chloro benzoxazole (101 mg, 0.66 mmol). The mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude mixture water was added and extracted with ethyl acetate. The organic layer was dried over anhydride sodium sulfate, filtered and concentrated to obtain a solid which was purified by flash column chromatography (eluent: 3% methanol in chloroform) to yield the title compound (250 mg, 80%). [LCMS RtE=1.75 min, [M+H]+=569.1].

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionTo the crude mixture water was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydride sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a solid which
  9. customwas purified by flash column chromatography (eluent: 3% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-5121801bd2434ee4915702571a1cfb49
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530648B2

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