2-Chlorocyclopentanone → HCID 86624684, Verbindung

HRID 604889

Reaktionsgleichung

Reaktionsgleichung von HRID 604889
Cl[CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]([NH2:25])=[S:24])[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1>C(O)C.O1CCOCC1>[S:24]1[C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[N:25]=[C:23]1[NH:22][C:12]1[CH:13]=[CH:14][C:15]([N:16]2[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]2)=[C:10]([O:9][CH3:8])[CH:11]=1

Komponenten

5

Edukt 2

HCID 127512-ChlorocyclopentanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Produkt 1

HCID 86624684HCID 86624684, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The title compound was prepared in analogy to example 1 step e) from 40 mg (0.33 mmol) 2-chlorocyclopentanone and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea in ethanol (1.5 ml) and dioxane (1.5 ml). The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 41 mg (42%) (5,6-dihydro-4H-cyclopentathiazol-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light yellow solid. MS ISP (m/e): 327.3 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.25 (s, 1H), 7.64 (s, 1H), 7.44 (s, 1H), 7.32 (d, 1H), 7.23 (d, 1H), 7.01 (s, 1H), 3.78 (s, 3H), 2.78 (br t, 2H), 2.67 (br t, 2H), 2.35 (m, 2H), 2.14 (s, 3H).

Aufarbeitung

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 41 mg (42%) (5,6-dihydro-4H-cyclopentathiazol-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-cc5873822b76497ba47a64eb0645e7a6
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910740B2

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