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

HRID 2244986Notes

Reaction equation

HRID 2244986 reaction equation
CN1CCN=C1[C:7]1[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][CH:8]=1.[CH3:35][N:36]([N:38]=C1C=CC(N)=CC1)[CH3:37].C(Cl)CCl>CN(C=O)C.O>[CH3:35][N:36]([N:38]=[C:7]1[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][CH2:8]1)[CH3:37]

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 686968834-(Dimethylaminoimino)phenylamine

Product 1

HCID 68693326N-[4-(dimethylaminoimino)phenyl]-2-(2-bromophenyl)-2-(4-chlorophenylamino-carbonylamino)-acetamideYield 48.4%

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-(dimethylaminoimino)phenylamine (51 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 (40 mg). MS 528.2 and 530.2 (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-0d789329ed6041e2a73f67a9973e3044
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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