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

HRID 1665675

Reaction equation

HRID 1665675 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

HCID 57875815N-biphenyl-4-yl-2-Methyl-malonamic acid methyl esterYield 77.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-455ba1db926f4928b12bd1c295bb1b98
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Linked notes

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