1-Hydroxybenzotriazole → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide

HRID 1665651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665651
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:26]2[N:31]=[CH:30][C:29]([NH:32][C:33](=[O:38])[CH2:34][C:35]([OH:37])=O)=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl.[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.O>[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[C:59]([N:61]1[CH2:62][CH2:63][N:64]([C:35](=[O:37])[CH2:34][C:33]([NH:32][C:29]2[CH:30]=[N:31][C:26]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:27][CH:28]=2)=[O:38])[CH2:65][CH2:66]1)=[O:60]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874490N-(6-phenyl-pyridin-3-yl)-malonamic acidHCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

Produkt 1

HCID 442314473-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamideAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

HOBt (41 mg, 0.3 mmol) and DIEA (98 mg, 0.76 mmol) were added to a stirred solution of N-(6-phenyl-pyridin-3-yl)-malonamic acid (65 mg, 0.25 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (58 mg, 0.3 mmol) followed by (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (93 mg, 0.3 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 58.5 mg (46%) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LCMS: 507.1 (M+1)+ 98.54%, 1H NMR: (DMSO-d6): δ 10.5 (d, 1H), 8.8 (dd, 1H), 8.2-7.86 (m, 4H), 7.5 (d, 1H), 7.34 (m, 6H), 3.8-3.4 (m, 8H), 3.2-3.1 (m. 2H).

Aufarbeitung

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a139505b54de4929bc172bb427e27e58
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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