2-Bromobenzoic acid → N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

HRID 1665603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665603
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.Cl.[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52](=[O:59])[N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:45][CH:44]=1>CN(C=O)C.O>[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:44]=[CH:45][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52]([N:53]2[CH2:54][CH2:55][N:56]([C:23](=[O:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[Br:20])[CH2:57][CH2:58]2)=[O:59])=[CH:47][CH:48]=1

Komponenten

8

Edukt 5

HCID 69402-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66625265N-Biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride

Produkt 1

HCID 44230951N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionamideAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

HOBt (34 mg, 0.25 mmol) and DIPEA (67.9 mg, 0.51 mmol) were added to a stirred solution of 2-bromobenzoic acid (42 mg, 0.21 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (75 mg, 0.2 mmol) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water and the product extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated. The residue was purified by column chromatography using silica gel 60-120 mesh (80% ethyl acetate in hexane) to afford 35 mg (33%) of N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 506.10 (M+1)+ 96.5%, 1H NMR: (CDCl3): δ 9.6 (d, 1H), 7.6 (m, 6H), 7.35 (m, 5H), 4.0 (m, 1H), 3.74 (m, 4H), 3.54 (d, 2H), 3.3 (m, 2H).

Aufarbeitung

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-923b0d17fb2748ceb991824678021a47
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

Notizen zur Reaktion

Wird geladen…