Water → [2'-({[1-(2,4-Dichloro-phenyl)-cyclopropanecarbonyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester

HRID 1810395Notes

Reaction equation

HRID 1810395 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12](Cl)=[O:13])[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH2:22]([O:24][C:25](=[O:49])[CH2:26][C:27]1[CH:28]=[C:29]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2[CH2:45][NH:46][CH2:47][CH3:48])[C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)[CH3:23].O>C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:49])[CH2:26][C:27]1[CH:28]=[C:29]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][C:36]=2[CH2:45][N:46]([C:12]([C:9]2([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH2:11][CH2:10]2)=[O:13])[CH2:47][CH3:48])[C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine3×HCID 30192901-(2,4-Dichlorophenyl)cyclopropanecarbonyl chlorideHCID 66604101(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66607414[2'-({[1-(2,4-Dichloro-phenyl)-cyclopropanecarbonyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-(2,4-dichloro-phenyl)-cyclopropanecarbonyl chloride (0.37 mmol) in CH2Cl2 was added triethylamine (0.16 mL, 1.12 mmol), and the mixture was stirred for 10 minutes. (2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.146 g, 0.37 mmol) in CH2Cl2 was then added, and the reaction was stirred for 30 minutes at room temperature. Additional triethylamine (0.1 mL, 0.72 mmol) was added, and the reaction was stirred for another 30 minutes. Analytical LCMS indicated that starting material was still present, so another portion of triethylamine (0.1 mL, 0.72 mmol) was added, and the reaction was stirred for 1 hour and then worked-up with CH2Cl2 and H2O. The combined organic layers were dried and concentrated, and the residue was purified by silica gel chromatography (10-40% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred for 30 minutes at room temperature
  2. stirringthe reaction was stirred for another 30 minutes
  3. stirringthe reaction was stirred for 1 hour
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (10-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e34e7289bd143a79f6464bd466b03b9
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

Loading…