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Diisopropylethylamine → 4-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178109
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Reaktionsgleichung

Reaktionsgleichung von HRID 1178109
Cl.[C:2]1([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[NH2:35][CH2:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45](=[O:56])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]([F:55])([F:54])[F:53])[CH2:41][CH2:40]1)=[O:38]>C(Cl)Cl.O>[O:38]=[C:37]([N:39]1[CH2:40][CH2:41][N:42]([C:45](=[O:56])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]([F:55])([F:53])[F:54])[CH2:43][CH2:44]1)[CH2:36][NH:35][C:23]([N:10]1[CH:9]=[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=[N:11]1)=[O:25]
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Komponenten

7

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 665923304-phenyl-1H-pyrazole hydrochlorideHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Produkt 1

HCID 251655334-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Ausbeute 32,97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A mixture of 4-Phenyl-1H-pyrazole hydrochloride salt (prepared by the method described above)(44 mg, 0.3 mmol), DIPEA (88 mg, 0.119 ml, 0.685 mmol) and DCM (2 ml) was added to a stirred solution of triphosgene (36 mg, 0.12 mmol) in DCM (1 mL) at room temperature. After 30 minutes, to the above solution, a mixture of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above)(108 mg, 0.3 mmol), DIPEA (88 mg, 0.119 ml, 0.685 mmol) and DCM (2 ml) was added and the resulting mixture was stirred at room temperature for 30 minutes. 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 get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 30-70% EtOAc in Hexane as eluent) to afford 48.8 mg (32.97% yield) 4-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.25%. 1H NMR (CDCl3): δ 8.48-8.4 (d, 1H), 8.04-7.98 (bs, 1H), 7.96-7.92 (s, 1H), 7.8-7.74 (d, 1H), 7.7-7.58 (m, 2H), 7.56-7.5 (d, 2H), 7.44-7.1 (m, 4H), 4.38-4.3 (d, 2H), 4.28-4.2 (t, 1H), 4.1-4.0 (bs, 1H), 3.82-3.66 (m, 2H), 3.64-3.5 (m, 2H), 3.46-3.38 (t, 1H),), 3.32-3.2 (s, 2H).

Aufarbeitung

  1. customprepared by the method
  2. customprepared by the method
  3. additionwas added
  4. extractionthe product was extracted with EtOAc
  5. washthe organic layer was washed with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto get the residue
  9. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 30-70% EtOAc in Hexane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-0a1def37a07249e189cfd964ab461502
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842696B2

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