1,2-Dichloroethane → N-[4-(pyrrolidin-1-ylimino)phenyl]-2-(2-bromophenyl)-2-(4-chlorophenylamino-carbonylamino)-acetamide

HRID 2244987Notes

Reaction equation

HRID 2244987 reaction equation
CN1CCN=C1C1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:34])[CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Br:33])[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:18])=[CH:9]C=1.[N:35]1([N:40]=[C:41]2C=CC(N)=C[CH2:42]2)[CH2:39][CH2:38][CH2:37][CH2:36]1.C(Cl)CCl>CN(C=O)C.O>[N:35]1([N:40]=[C:41]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:34])[CH:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Br:33])[NH:16][C:17]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)=[O:18])=[CH:9][CH2:42]2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 11692377N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideHCID 686963124-(Pyrrolidinylimino)phenylamine

Product 1

HCID 68694678N-[4-(pyrrolidin-1-ylimino)phenyl]-2-(2-bromophenyl)-2-(4-chlorophenylamino-carbonylamino)-acetamideYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (from EXAMPLE 77, 60 mg, 0.16 mmol) and 4-(pyrrolidin-1-ylimino)phenylamine (60 mg, 0.31 mmol) in DMF (4 mL) and H2O (1 mL), EDC (120 mg, 0.62 mmol) was added. After being stirred at room temperature for 2 h, the mixture was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (70 mg). MS 554.2 and 556.2 (M+H, Cl+Br pattern).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-7dc1c061c8b74dc188afca3b350e3ab4
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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