Phosphorus oxychloride → N-[4-(2-dimethylaminomethyl-phenyl)phenyl]-2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244980Notes

Reaction equation

HRID 2244980 reaction equation
[F: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.[CH3:23][N:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH3:25].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:25][N:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:9](=[O:11])[CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F: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:37][CH:38]=1)[CH3:23]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 588976922'-Dimethylaminomethylbiphenyl-4-ylamineHCID 68695741HCID 68695741, compound

Product 1

HCID 11720698N-[4-(2-dimethylaminomethyl-phenyl)phenyl]-2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 7.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (60 mg, 0.19 mmol) and 4-(2-dimethylaminomethyl-phenyl)phenylamine (50 mg, 0.22 mmol) in pyridine (3 mL) cooled in an ice-bath, POCl3 (0.034 mL, 0.37 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (8 mg). MS 531.1 and 533.1 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-a49f3ab9fdcf43e38fa8f2ab76fd8e31
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…