4-Aminobiphenyl → HCID 57875826, compound

HRID 1665671Notes

Reaction equation

HRID 1665671 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:23][O:24][C:25](=[O:31])[CH:26]([F:30])[C:27](O)=[O:28].[C:32]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:23][O:24][C:25](=[O:31])[CH:26]([F:30])[C:27]([NH:38][C:35]1[CH:34]=[CH:33][C:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:37][CH:36]=1)=[O:28]

Participants

8

Reactant 4

HCID 71024-AminobiphenylHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15176477HCID 15176477, compound

Product 1

HCID 57875826HCID 57875826, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBt (83 mg, 0.61 mmol), DMAP (125 mg, 1.02 mmol) and EDCI.HCl (118 mg, 0.61 mmole) were added to a stirred solution of 2-fluoro-malonic acid monomethyl ester (70 mg, 0.514 mmol) in DMF (2 mL). Biphenyl-4-ylamine (100 mg, 0.61 mmol) was then added and the resulting mixture was stirred at ambient temperature overnight. The mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 114 mg (80%) of N-biphenyl-4-yl-2-fluoro-malonamic acid methyl ester

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad9a6c8705e64acd8dc02ca4bb014113
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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