Water → (S)-5-Oxopyrrolidine-3-carboxylic acid{1-(2-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-yl}amide

HRID 83542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83542
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[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]=2)=[CH:11][C:10]([NH2:28])=[N:9]1.[O:29]=[C:30]1[NH:34][CH2:33][C@@H:32]([C:35](O)=[O:36])[CH2:31]1.CCN=C=NCCCN(C)C.Cl.O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[C:17]([CH2:19][O:20][C@H:21]([CH3:26])[C:22]([F:23])([F:24])[F:25])[CH:16]=[C:15]([F:27])[CH:14]=2)=[CH:11][C:10]([NH:28][C:35]([C@H:32]2[CH2:31][C:30](=[O:29])[NH:34][CH2:33]2)=[O:36])=[N:9]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25100087(S)-5-oxopyrrolidine-3-carboxylic acidHCID 866803741-(2-Fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine

Produkt 1

HCID 71287722(S)-5-Oxopyrrolidine-3-carboxylic acid{1-(2-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-yl}amideAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-fluorophenyl)-5-[3-fluoro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-1H-pyrazol-3-ylamine (about 0.125 mmol) prepared in the previous step in dimethylformamide (0.5 ml) were sequentially added (S)-5-oxopyrrolidine-3-carboxylic acid (18 mg) prepared in Preparation 14 and WSC.HCl (29 mg) at room temperature, and the mixture was stirred for 3 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was concentrated under reduced pressure, and the resulting residue 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 (32 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThis organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)
  4. additionTo the resulting solid were added water
  5. stirringa small amount of methanol, and the mixture was stirred
  6. filtrationA solid was collected from this suspension by filtration
  7. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b91a8e785c554299948de12d14a2ca2b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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