Phosphorus oxychloride → N-[4-(pyrrolidin-1-ylcarbonyl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244993Notes

Reaction equation

HRID 2244993 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.Cl.[N:24]1([C:29]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[N:24]1([C:29]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][C:9](=[O:11])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:14])=[CH:35][CH:36]=2)=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 686898412-(2-Methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acidHCID 686922284-(Pyrrolidinylcarbonyl)phenylamine hydrochloride

Product 1

HCID 11569430N-[4-(pyrrolidin-1-ylcarbonyl)phenyl]-2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 19.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(2-methylphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (50 mg, 0.16 mmol) and 4-(pyrrolidinylcarbonyl)phenylamine hydrochloride (43 mg, 0.19 mmol) in pyridine (3 mL) cooled in ice-bath, POCl3 (0.028 mL, 0.31 mmol) was added. The 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 (15 mg). MS 491.4 and 493.4 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-b65c4c795b344d728c39f31b71a43a49
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…