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

HRID 2244981Notes

Reaction equation

HRID 2244981 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])=[C:35]([F:40])[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:38]=[CH:37][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])=[C:35]([F:40])[CH:34]=1)[CH3:23]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 179781624-(2-Dimethylaminomethyl-phenyl)-2-fluoro-phenylamineHCID 686957412-(2-Fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid

Product 1

HCID 11713702N-[4-(2-dimethylaminomethyl-phenyl)-2-fluorophenyl]-2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 24.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (from EXAMPLE 55, 90 mg, 0.28 mmol) and 4-(2-dimethylaminomethyl-phenyl)-2-fluoro-phenylamine (80 mg, 0.33 mmol) in pyridine (3 mL) cooled in an ice-bath, POCl3 (0.050 mL, 0.55 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 (38 mg). MS 549.1 and 551.2 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-7df17864253f440590ce2bea7bee265c
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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