1-Hydroxybenzotriazole → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamide

HRID 1665683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665683
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:20]=[C:19]([NH:21][C:22](=[O:27])[CH2:23][C:24]([OH:26])=O)[O:18][N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)=[O:47]>CN(C=O)C.O>[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([N:48]1[CH2:49][CH2:50][N:51]([C:24](=[O:26])[CH2:23][C:22]([NH:21][C:19]2[O:18][N:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:20]=2)=[O:27])[CH2:52][CH2:53]1)=[O:47]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57875817N-(3-phenyl-isoxazol-5-yl)-malonamic acidHCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

Produkt 1

HCID 442316833-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamideAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (69.2 mg, 0.55 mmol) was added to a stirred solution of N-(3-phenyl-isoxazol-5-yl)-malonamic acid (45 mg, 0.18 mmol) in DMF (2 mL) followed by HOBt (29 mg, 0.22 mmol). After 2 minutes of stirring, (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (67 mg, 0.22 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 38.9 mg (43.22% Yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamide. LC/MS [M+1]+: 497.07, 97.0%. 1H NMR: (300 MHz, DMSO-d6): δ 11.8 (bs, 1H), 7.92-7.8 (m, 2H), 7.5 (d, 1H), 7.6-7.3 (m, 6H), 6.8-6.7 (d, 1H), 3.8-3.4 (m, 8H), 3.24-3.04 (m, 2H).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at ambient temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db137e823b9a477d9af9d5844aee295d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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