StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177917
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1177917
CCN(C(C)C)C(C)C.Cl.[NH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:17][CH2:16]1)=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:54][C:55]1[N:59]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[N:58]=[CH:57][C:56]=1[C:66](O)=[O:67]>CN(C=O)C.O>[O:14]=[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:29])[F:30])[CH2:19][CH2:20]1)[CH2:12][NH:11][C:66]([C:56]1[CH:57]=[N:58][N:59]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:55]=1[CH3:54])=[O:67]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1452215-Methyl-1-phenylpyrazole-4-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Produkt 1

HCID 25166501
5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Ausbeute 11,74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (189 mg, 0.256 mL, 1.48 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above) (208 mg, 0.59 mmol) in DMF (2 mL). HOBT (80 mg, 0.59 mmol) and EDCI (114 mg, 0.59 mmol) were then added at room temperature. After 2 minutes, 5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid (100 mg, 0.49 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 29 mg (11.74% yield) 5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 94.32%. 1H NMR (DMSO-d6): δ 8.24 (bs, 1H), 8.14 (s, 1H), 7.88-7.74 (m, 2H), 7.7-7.6 (m, 1H), 7.6-7.4 (m, 6H), 4.2-4.4 (d, 2H), 3.9-3.6 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.0 (m, 2H).

Aufarbeitung

  1. customprepared by the method
  2. extractionthe product was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60da7f74c019458ab7b4b6233c7cc6dd
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842696B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion