2-[(3-Chlorophenyl)formamido]acetic acid → 3-Chloro-N-{2-[3-(3-chloro-2-methyl-1-methylene-but-2-enyl)-4-oxo-imidazolidin-1-yl]-2-oxo-ethyl}-benzamide

HRID 507387Notes

Reaction equation

HRID 507387 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][NH:10][CH2:9]2)[CH:5]=C[CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[C:19]([NH:21][CH2:22][C:23](O)=[O:24])=[O:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[C:19]([NH:21][CH2:22][C:23]([N:10]1[CH2:11][C:12](=[O:13])[N:8]([C:4](=[CH2:5])[C:3]([CH3:14])=[C:2]([Cl:1])[CH3:7])[CH2:9]1)=[O:24])=[O:20]

Participants

5

Reactant 3

HCID 4482-[(3-Chlorophenyl)formamido]acetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594340313-(3-Chloro-2-methyl-phenyl)-imidazolidin-4-one

Product 1

HCID 866243223-Chloro-N-{2-[3-(3-chloro-2-methyl-1-methylene-but-2-enyl)-4-oxo-imidazolidin-1-yl]-2-oxo-ethyl}-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-Chloro-2-methyl-phenyl)-imidazolidin-4-one (360 mg, 1.7 mmol, 1 eq), (3-Chloro-benzoylamino)-acetic acid (365 mg, 1.7 mmol, 1 eq), BOP (909 mg, 2.05 mmol, 1.2 eq), and TEA (0.88 ml) in DMF (5 ml) was stirred at room temperature overnight. It was purified with HPLC to give the desired product. LCMS observed for (M+H)+: 406.1

Workup

  1. customIt was purified with HPLC

Sources & evidence

ORD record
ord-0a6dbd86b1c04a71a54a40025b31bd03
Source dataset
uspto-grants-2010_08
Patent number
US07786157B2

Reaction notes

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