4-Bromophenacyl bromide → 8-(4-(4-Bromophenyl)thiazol-2-yl)-3-methylimidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

HRID 570926

Reaktionsgleichung

Reaktionsgleichung von HRID 570926
[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12](=[S:14])[NH2:13])=[C:5]2[N:4]=[N:3]1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=1)=O>CC#N>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:13]=[C:12]([C:11]3[N:10]=[CH:9][N:6]4[C:7](=[O:8])[N:2]([CH3:1])[N:3]=[N:4][C:5]=34)[S:14][CH:16]=2)=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 74544-Bromophenacyl bromideHCID 33528803-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide

Produkt 1

HCID 498705188-(4-(4-Bromophenyl)thiazol-2-yl)-3-methylimidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide (0.48 mmol) and 2,4′-dibromoacetophenone (0.48 mmol) were stirred in MeCN overnight at room temperature. A slight yellow solid persisted which was filtered off before the remaining mixture was purified by preparative thin layer chromatography, eluting with 10% MeCN/DCM, to give the title compound. Yield=81%. δH (DMSO-d6): 8.92 (1H, s), 8.39 (1H, s), 8.04 (2H, d, J=8.8), 7. (2H, d, J=8.8), 3.89 (3H, s).

Aufarbeitung

  1. filtrationwas filtered off before the remaining mixture
  2. customwas purified by preparative thin layer chromatography
  3. washeluting with 10% MeCN/DCM

Quellen und Nachweise

ORD-Eintrag
ord-a1c3fa3b00fe4c8ba3855531d8f9c6c2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024018B2

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