4-Aminobiphenyl → 1-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester

HRID 1665668

Reaction equation

HRID 1665668 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]([C:40]1([C:43](O)=[O:44])[CH2:42][CH2:41]1)=[O:39]>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:36][O:37][C:38]([C:40]1([C:43](=[O:44])[NH:29][C:26]2[CH:25]=[CH:24][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][CH:27]=2)[CH2:42][CH2:41]1)=[O:39]

Participants

8

Reactant 4

HCID 71024-AminobiphenylHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 578758101-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl esterYield 75.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBt (70 mg, 0.54 mmol), DMAP (110 mg, 0.9 mmol), EDCI.HCl (104 mg, 0.54 mmol) followed by biphenyl-4-ylamine (92 mg, 0.54 mmol) were added to a stirred solution of cyclopropane-1,1-dicarboxylic acid methyl ester (65 mg, 0.45 mmol) in DMF (2 mL) and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with water. The resulting precipitate was isolated by filtration and dried to afford 100 mg (75%) of 1-(biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-735d1618010c41a1a8d9c6a5a3a1ae4d
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Linked notes

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