Water → (S)-5-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

HRID 1672833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672833
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[N:24]=[N:25][NH:26][N:27]=4)[CH:18]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:28]=1.[C:29](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[CH3:29][N:25]1[N:26]=[N:27][C:23]([C:19]2[CH:18]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:28]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:22]=[CH:21][CH:20]=2)=[N:24]1.[CH3:29][N:27]1[C:23]([C:19]2[CH:18]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:28]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:22]=[CH:21][CH:20]=2)=[N:24][N:25]=[N:26]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67350905(S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

Produkt 2

HCID 67350039(S)-5-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-oneAusbeute 15 %HCID 67351301(S)-5-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-oneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-9-Methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (283 mg, 0.717 mmol) obtained in Step 1 was dissolved in DMF (7 mL), and the mixture was stirred at room temperature for 2 hours after adding potassium carbonate (149 mg, 1.08 mmol) and methyl iodide (0.0670 mL, 1.08 mmol). Thereafter, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give (S)-5-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (221 mg, 75%) and (S)-5-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (44.9 mg, 15%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe residue obtained upon concentration under reduced pressure
  4. customwas then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-66377dbf5842474a8a91c67fcfcc3865
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998954B2

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