Methane → HCID 178508343, Verbindung

HRID 646735Notizen

Reaktionsgleichung

[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1.[C:18]([NH:26][NH2:27])(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C=O)C.C>CCOC(C)=O.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:16]1[NH:17][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][N:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 190 °C

Versuchsvorschrift

A mixture of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (0.11 g, 0.5 mmol) and benzoic hydrazide (0.15 g, 1 mmol) were heated at 180-200° C. for 30 min. After cooling, the reaction mass was taken up with 5 mL DMF and the obtained solution was diluted with EtOAc and water, clarified with charcoal and filtered on Celite. The organic layer was separated. After drying over sodium sulfate, the ethyl acetate was evaporated under reduced pressure. Purification of the residue by preparative HPLC (Acetonitrile/water) gave desired product (50 mg): 1H NMR (400 MHz; DMSO-d6): 8.3 (s, 1H); 8.1 (m, 2H); 7.6-7.3 (m, 7H); 5.45 (t, 1H); 4.6 (d, 2H); MS (EI) for C23H22N5OF3 HCl: 442 (MH+).

Aufarbeitung

temperatureAfter cooling
filtrationfiltered on Celite
customThe organic layer was separated
dry with materialAfter drying over sodium sulfate
customthe ethyl acetate was evaporated under reduced pressure
customPurification of the residue by preparative HPLC (Acetonitrile/water)

Quellen und Nachweise

ORD-Eintrag: ord-1d31dba7f196450bbc106bb2d5fa2cc2
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07704995B2

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