4-Aminobiphenyl → N-biphenyl-4-yl-2-Methyl-malonamic acid methyl ester

HRID 1665675

Reaktionsgleichung

Reaktionsgleichung von HRID 1665675
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.[CH3:36][O:37][C:38](=[O:44])[CH:39]([CH3:43])[C:40](O)=[O:41]>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:36][O:37][C:38](=[O:44])[CH:39]([CH3:43])[C:40]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:28][CH:27]=1)=[O:41]

Komponenten

8

Edukt 4

HCID 71024-AminobiphenylHCID 757711-HydroxybenzotriazoleHCID 3006933-Methoxy-2-methyl-3-oxopropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 57875815N-biphenyl-4-yl-2-Methyl-malonamic acid methyl esterAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HOBt (245 mg, 1.8 mmol), DMAP (370 mg, 3.0 mmol), EDCI.HCl (348 mg, 1.8 mmol) followed by biphenyl-4-ylamine (307 mg, 1.8 mmol) were added to a stirred solution of 2-methyl-malonic acid monomethyl ester (200 mg, 1.5 mmol) in DMF (3 mL) and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution and concentrated under reduced pressure to afford 330 mg (77%) of N-biphenyl-4-yl-2-Methyl-malonamic acid methyl ester.

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine solution
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-455ba1db926f4928b12bd1c295bb1b98
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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