Ethyl Acetate → 1-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea

HRID 347456

Reaktionsgleichung

Reaktionsgleichung von HRID 347456
NC1C=CC(O)=C(F)C=1.FC1C=CC(CC(SC#N)=O)=CC=1.[F:23][C:24]1[CH:25]=[C:26]([NH:43][C:44]([NH:46][C:47](=[O:56])[CH2:48][C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=2)=[S:45])[CH:27]=[CH:28][C:29]=1[O:30]C1C2=C(C)C(OC)=CN2N=CN=1.CCOC(C)=O>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([NH:43][C:44]([NH:46][C:47](=[O:56])[CH2:48][C:49]2[CH:50]=[CH:51][C:52]([F:55])=[CH:53][CH:54]=2)=[S:45])[CH:27]=[CH:28][C:29]=1[OH:30]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 116271861-(3-Fluoro-4-(6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaHCID 21081546HCID 21081546, Verbindung

Produkt 1

HCID 210814951-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-2-fluorophenol (50 mg, 0.3 mmol, Indofine Chemical Co.) in CH2Cl2 (5 mL) was added a 0.25 M solution of 2-(4-fluorophenyl)-1-thiocyanatoethanone (prepared using a similar procedure for the synthesis of Compound A of Example 2) in EtOAc (1.6 mL, 0.4 mmol). The reaction was stirred at room temperature for 20 minutes, concentrated in vacuo and purified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2) to give the title compound (100 mg, 95%) as a white solid.

Aufarbeitung

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-136b669c08d84bff8d58a9aded2b89e0
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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