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

HRID 1177890
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1177890
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]([OH:18])=O)[CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:41][CH2:42][C:43]([N:45]1[CH2:50][CH2:49][N:48]([C:51](=[O:62])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:60])[F:59])[CH2:47][CH2:46]1)=[O:44]>CN(C=O)C.O>[O:44]=[C:43]([N:45]1[CH2:46][CH2:47][N:48]([C:51](=[O:62])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:60])[F:59])[CH2:49][CH2:50]1)[CH2:42][NH:41][C:16]([C:13]1[CH:12]=[C:11]([CH3:10])[O:15][N:14]=1)=[O:18]
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Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Produkt 1

HCID 59559639
5-Methyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Ausbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (82.66 mg, 0.09 mL, 0.63 mmol) was added to a stirred solution of 5-methyl-isoxazole-3-carboxylic acid (32.52 mg, 0.25 mmol) in DMF (2 mL). HOBT (34.53 mg, 0.25 mmol) and EDCI (48.9 mg, 0.25 mol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (75 mg, 0.21 mmol) was added and the resulting mixture was stirred at room temperature overnight. 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 60-120 silica gel and 80% EtOAC in hexane as eluent) to afford 53 mg (58.62% yield) of 5-methyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 88.47%. 1H NMR (DMSO-d6): δ 8.55 (s, 1H), 7.88-7.74 (m, 2H), 7.74-7.62 (m, 1H), 7.6-7.5 (s, 1H), 6.75 (s, 1H), 4.22-4.4 (dd, 2H), 3.8-3.64 (m, 2H), 3.64-3.52 (s, 3H), 3.5-3.36 (m, 3H), 3.22-3.0 (m, 3H), 2.48-2.44 (s, 3H).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using 60-120 silica gel and 80% EtOAC in hexane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-7388a9950adb4b8d9939ff799faa15c0
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842696B2

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