1,2-Dichloroethane → N-[4-(3-oxo-morpholin-4-yl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244995Notes

Reaction equation

HRID 2244995 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[O:14])[C:9]([OH:11])=O.[O:23]=[C:24]1[CH2:29][O:28][CH2:27][CH2:26][N:25]1[C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1.C(Cl)CCl>CN(C=O)C>[O:23]=[C:24]1[CH2:29][O:28][CH2:27][CH2:26][N:25]1[C:30]1[CH:31]=[CH:32][C:33]([NH:36][C:9](=[O:11])[CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[O:14])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 686898412-(2-Methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid

Product 1

HCID 11691709N-[4-(3-oxo-morpholin-4-yl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (26 mg, 0.082 mmol) and 4-(3-oxo-morpholin-4-yl)phenylamine (23 mg, 0.12 mmol) in DMF (3 mL), EDC (39 mg, 0.20 mmol) was added. The reaction mixture was stirred at room temperature overnight. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a white powder (27 mg). MS 493.2 and 495.2 (M+H, Cl pattern).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-2bd7f7894d5a48f8bdc52212936691a5
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…