Phosphorus oxychloride → N-[4-(2-dimethylaminomethyl-imidazol-1-yl)-2-fluorophenyl]-2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244982Notes

Reaction equation

HRID 2244982 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[N:28]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([F:39])[CH:33]=2)[CH:29]=[CH:30][N:31]=1)[CH3:25].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:25][N:24]([CH2:26][C:27]1[N:28]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:9](=[O:11])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:14])=[C:34]([F:39])[CH:33]=2)[CH:29]=[CH:30][N:31]=1)[CH3:23]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 98780134-(2-Dimethylaminomethyl-imidazol-1-YL)-2-fluoro-phenylamineHCID 686957412-(2-Fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid

Product 1

HCID 11671074N-[4-(2-dimethylaminomethyl-imidazol-1-yl)-2-fluorophenyl]-2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 18.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-fluorophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (from EXAMPLE 55, 62 mg, 0.19 mmol) and 4-(2-dimethylaminomethyl-imidazol-1-yl)-2-fluorophenylamine (45 mg, 0.19 mmol) in pyridine (3 mL) cooled in an ice-bath, POCl3 (0.035 mL, 0.38 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 (19 mg). MS 539.1 and 541.1 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-f399087b0be7470e98dca08e600510ad
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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