3-Chloro-4-(3-chlorophenyl)-2-butanone → 5-[5-(3-Chloro-benzyl)-4-methyl-thiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrile

HRID 604869

Reaktionsgleichung

Reaktionsgleichung von HRID 604869
Cl[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[C:3](=O)[CH3:4].[C:14]([C:16]1[CH:17]=[C:18]([NH:28][C:29]([NH2:31])=[S:30])[CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1)#[N:15]>>[Cl:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH2:6][C:2]1[S:30][C:29]([NH:28][C:18]2[CH:19]=[CH:20][C:21]([N:22]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]3)=[C:16]([CH:17]=2)[C:14]#[N:15])=[N:31][C:3]=1[CH3:4]

Komponenten

3

Edukt 2

HCID 42509853-Chloro-4-(3-chlorophenyl)-2-butanoneHCID 86624673[3-Cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea

Produkt 1

HCID 251072575-[5-(3-Chloro-benzyl)-4-methyl-thiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrile

Versuchsvorschrift

The title compound was prepared in analogy to example 1 step e) from 54 mg (0.25 mmol) 3-chloro-4-(3-chlorophenyl)-2-butanone and 64 mg (0.25 mmol) [3-cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 50 mg (48%) 5-[5-(3-chloro-benzyl)-4-methyl-thiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrile as a light yellow solid. MS ISP (m/e): 420.1/422.2 (100/38) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.55 (s, 1H), 8.24 (s, 1H), 7.89 (s, 1H), 7.88 (d, 1H), 7.55 (d, 1H), 7.36-7.20 (m, 5H), 4.03 (s, 2H), 2.27 (s, 3H), 2.18 (s, 3H).

Aufarbeitung

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 50 mg (48%) 5-[5-(3-chloro-benzyl)-4-methyl-thiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrile as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-19477f088ae042a5b00881c70d1383ad
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910740B2

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