Hydrazine hydrate (1:1) → HCID 178423567, Verbindung

HRID 560854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560854
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:16]=3)[C:10]2=[O:29])=[N:6][C:5]=1[CH3:30])(=O)[CH3:2].CO[C:33](OC)([N:35](C)C)[CH3:34].O.[NH2:41]N>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:30][C:5]1[N:6]=[C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)=[O:22])=[CH:19][CH:20]=3)[C:10]2=[O:29])[S:8][C:4]=1[C:1]1[NH:41][N:35]=[C:33]([CH3:34])[CH:2]=1

Komponenten

6

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

Produkt 1

HCID 178423567HCID 178423567, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one (0.43 g, 1.00 mmol) in N,N-dimethylacetamide (5 mL) was added N,N-dimethylacetamide dimethyl acetal (0.5 mL, 3.40 mmol). The reaction mixture was heated for 24 hours at 110° C., and hydrazine monohydrate (0.30 mL, 6.18 mmol) was added. The reaction mixture was heated for another 10 minutes at 110° C., then cooled to ambient temperature, diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a colorless solid in 46% yield (0.25 g): mp 182-183° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 7.38-7.30 (m, 4H), 6.16 (s, 1H), 4.49 (s, 2H), 4.10-4.04 (m, 2H), 3.68 (br s, 2H), 3.46-3.31 (m, 4H), 2.46 (s, 3H), 2.32 (s, 3H), 1.56-1.49 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 169.9, 156.6, 155.8, 143.6, 137.3, 136.1, 128.2, 127.4, 104.2, 48.7, 47.7, 41.8, 26.5, 25.6, 24.5, 21.1, 16.5: MS (ES+) m/z 465.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated for another 10 minutes at 110° C.
  2. temperaturecooled to ambient temperature
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-504eb39c800843909f18a0fab9365d7b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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