Triethylamine → [2'-({[2-(4-Chloro-phenoxy)-2-methyl-propionyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 563630Notes

Reaction equation

HRID 563630 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:41])[CH2:18][C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=2[CH2:37][NH:38][CH2:39][CH3:40])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:15][O:16][C:17](=[O:41])[CH2:18][C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:29][C:28]=2[CH2:37][N:38]([C:8](=[O:9])[C:7]([O:6][C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=2)([CH3:12])[CH3:11])[CH2:39][CH3:40])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chlorideHCID 66603748(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66604389[2'-({[2-(4-Chloro-phenoxy)-2-methyl-propionyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-phenoxy)-2-methyl-propionyl chloride (0.58 mmol) in CH2Cl2 was added (2′-ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.200 g, 0.52 mmol) in triethylamine (0.17 mL, 1.23 mmol), and the reaction was stirred at room temperature for 30 minutes. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a60d5955f83e4976a0853075a9065487
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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