O-Methyltyramine → HCID 23090906, compound

HRID 1819998Notes

Reaction equation

HRID 1819998 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH:11][CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:26])=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 4657O-MethyltyramineHCID 757711-HydroxybenzotriazoleHCID 6160024-Biphenylcarboxylic acid, 4'-chloro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 23090906HCID 23090906, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)ethaneamine (500 mg, 3.31 mmol), 4′-chloro[1,1′-biphenyl]-4-carboxylic acid (846 mg, 3.64 mmol) and 1-hydroxybenzotriazole (760 mg, 4.96 mmol) in dimethylformamide (10 ml) was added ethyldimethylaminopropylcarbodiimide hydrochloride (951 mg, 4.96 mmol) at 0° C., and the mixture was was stirred at room temperature for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with 1N aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give the title compound (1.03 g).

Workup

  1. washthe mixture was washed with 1N aqueous sodium hydroxide solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43c6fede63244d398d382923d8cc586f
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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