Ethylenediamine → HCID 71279840, Verbindung

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Reaktionsgleichung

[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][C:23]([CH3:26])=[CH:22]4)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.CCOCC>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][C:23]([CH3:26])=[CH:22]4)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a stirred solution of N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (60 mg, 126 μmol) in DMF (4 mL) was added ethylenediamine (355 mg, 399 μL, 5.9 mmol) then tetrabutylammonium fluoride (389 μL, 389 μmol). The solution was heated to 60° C. with stirring under a nitrogen atmosphere for 20 h. The reaction mixture was cooled, diluted with ether, washed water and brine, then dried (MgSO4), filtered, and concentrated in vacuo to give an oil which slowly crystallized. The crystals were triturated with water twice then dried under vacuum to give N-tert-butyl-2-(2-Methyl-1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (29 mg) as a yellow solid. MS (M+H)+=348.1; 1H NMR (CDCl3) δ: 8.87 (s, 1H), 8.35 (d, J=3.0 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.55-7.61 (m, 1H), 7.20-7.30 (m, 2H), 6.33-6.36 (m, 1H), 2.54 (s, 3H), 1.53 (s, 9H).

Aufarbeitung

temperatureThe reaction mixture was cooled
washwashed water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give an oil which
customslowly crystallized
customThe crystals were triturated with water twice
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-9eee3f7230eb4f6b862d937e295293ea
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658646B2

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