Water → HCID 68731776, Verbindung

HRID 1259311Notizen

Reaktionsgleichung

C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:8]=1[CH3:28])C.Cl.[NH:33]([C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1)[NH2:34].O>CO>[C:39]([C:38]1[CH:41]=[CH:42][C:35]([NH:33][N:34]=[CH:4][C:5]#[C:6][C:7]2[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=3)[C:8]=2[CH3:28])=[CH:36][CH:37]=1)#[N:40]

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

In a 100 mL round-bottomed flask, methyl 6-(3,3-diethoxyprop-1-ynyl)-5-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrazine-2-carboxylate (SM2, 1.136 g, 2.59 mmol) and 4-hydrazinylbenzonitrile hydrochloride (0.508 g, 3.00 mmol) were stirred in methanol (25 mL) and water (2.5 ml) under air at 65° C. After 1 h, the mixture was allowed to cool to 45° C., water (50 ml) was added and the mixture then cooled to RT. After stirring for 30 minutes, the solid was filtered off, washed with water (100 ml) and then air dried to give methyl 6-(3-(2-(4-cyanophenyl)hydrazono)prop-1-ynyl)-5-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrazine-2-carboxylate (1.18 g, 95%) as a yellow solid.

Aufarbeitung

customat 65° C
temperaturethe mixture then cooled to RT
filtrationthe solid was filtered off
washwashed with water (100 ml)
customair dried

Quellen und Nachweise

ORD-Eintrag: ord-741e31ed1aa04543ade2d05b14e35a8a
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08466284B2

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