1,1'-Carbonyldiimidazole → 4-(3-(Cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-B]pyrazin-5-YL)benzamide

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Reaktionsgleichung

Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.BrC1N=C([NH:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)C(N)=NC=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:36]>C1COCC1.CN(C=O)C>[CH:13]1([CH2:12][N:8]2[C:6]3[C:5](=[N:4][CH:3]=[C:2]([C:31]4[CH:32]=[CH:33][C:28]([C:27]([NH2:26])=[O:36])=[CH:29][CH:30]=4)[N:7]=3)[NH:10][C:9]2=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

6-Bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 6-Bromo-N2-(cyclohexylmethyl)pyrazine-2,3-diamine. (4.85 g, 17.01 mmol) was dissolved in THF (50 mL), 1,1′-carbonyldiimidazole (3.45 g, 21.26 mmol) was added, and the reaction solution was divided into 4 different vials. Each fraction was heated in a Biotage Emrys Optimizer microwave reactor at 120° C. for 30 min. The reacted fractions were combined and condensed under reduced pressure. The crude material was dissolved in minimal DMF and precipitated with deionized water while sonicating. The filtered product was dried in a vacuum oven at 60° C. over night to afford the title compound (4.72 g, 89%). MS (ESI) m/z 311.3 [M]+, 313.5 [M+2]+

Aufarbeitung

customcondensed under reduced pressure
customprecipitated with deionized water
customwhile sonicating
customThe filtered product was dried in a vacuum oven at 60° C. over night

Quellen und Nachweise

ORD-Eintrag: ord-1dba2384092e466082a40a1618a52903
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07981893B2

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