Perchloric Acid → [2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

HRID 29100

Reaktionsgleichung

Reaktionsgleichung von HRID 29100
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]([N+:16]#[C-:17])([CH3:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12].[Br:18][C:19]1[S:23][C:22]([CH:24]=O)=[CH:21][CH:20]=1.Cl(O)(=O)(=O)=O>C(Cl)(Cl)Cl>[Br:18][C:19]1[S:23][C:22]([C:24]2[N:1]=[C:2]3[CH:7]=[N:6][CH:5]=[CH:4][N:3]3[C:17]=2[NH:16][C:9]([CH3:15])([CH3:8])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 24247Perchloric AcidHCID 267251,1,3,3-Tetramethylbutyl isocyanideHCID 784285-Bromothiophene-2-carbaldehydeHCID 78747Aminopyrazine

Produkt 1

HCID 69316811[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4.76 g (50.0 mmol) of 2-aminopyrazine were dissolved together with 8.76 ml (50.0 mmol) of 1,1,3,3-tetramethyl-butylisonitrile and 5.42 ml (50.0 mmol) of 5-bromothiophene-2-carbaldehyde in chloroform (40 ml) After addition of perchloric acid (5 ml), the mixture was stirred at 50° C. for 16 h. After cooling to RT, washing was performed 2× with a sat. aq. sodium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DCM 1:3) with the group, 11.39 g (28.0 mmol, 56% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. washwashing
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a50e45d7d55499e974d1b28fd9e08c9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420056B2

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