1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (R)-2-Oxoimidazolidine-4-carboxylic acid{1-(4-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-yl}amide

HRID 83551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83551
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[C:17]([CH2:19][O:20][C@H:21]([CH3:26])[C:22]([F:25])([F:24])[F:23])[CH:16]=[C:15]([F:27])[CH:14]=3)=[CH:11][C:10]([NH2:28])=[N:9]2)=[CH:4][CH:3]=1.[O:29]=[C:30]1[NH:34][C@@H:33]([C:35](O)=[O:36])[CH2:32][NH:31]1.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[C:17]([CH2:19][O:20][C@H:21]([CH3:26])[C:22]([F:24])([F:25])[F:23])[CH:16]=[C:15]([F:27])[CH:14]=3)=[CH:11][C:10]([NH:28][C:35]([C@H:33]3[CH2:32][NH:31][C:30](=[O:29])[NH:34]3)=[O:36])=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7003745(4R)-2-oxoimidazolidine-4-carboxylic acidHCID 712878641-(4-Fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine

Produkt 1

HCID 71287732(R)-2-Oxoimidazolidine-4-carboxylic acid{1-(4-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-yl}amideAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine (about 0.277 mmol) prepared in the previous step in chloroform (1 ml) were sequentially added (R)-2-oxoimidazolidine-4-carboxylic acid (40 mg) and WSC.HCl (64 mg) at room temperature, and the mixture was stirred for 3 hours. This reaction mixture was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1). To the resulting solid were added water and a small amount of methanol, and the mixture was stirred. A solid was collected from this suspension by filtration and was dried under reduced pressure to give the titled compound (56 mg).

Aufarbeitung

  1. customat room temperature
  2. customThis reaction mixture was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)
  3. additionTo the resulting solid were added water
  4. stirringa small amount of methanol, and the mixture was stirred
  5. filtrationA solid was collected from this suspension by filtration
  6. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7774fef2fddd4f018d02e433035e7403
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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