1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-{2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionylamino}-2-methyl-phenyl)-propionic-acid Methyl Ester

HRID 860686Notes

Reaction equation

HRID 860686 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH:18]([CH3:22])[C:19](O)=[O:20])[CH3:2].[CH3:23][O:24][C:25](=[O:36])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][C:29]=1[CH3:35].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:23][O:24][C:25](=[O:36])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:19](=[O:20])[CH:18]([C:4]2[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:15])[F:17])=[CH:10][CH:9]=3)[S:7][C:3]=2[CH2:1][CH3:2])[CH3:22])=[CH:30][C:29]=1[CH3:35]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoateHCID 695896382-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid

Product 1

HCID 695893313-(4-{2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionylamino}-2-methyl-phenyl)-propionic-acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid (0.35 mmol), 3-(4-Amino-2-methyl-phenyl)-propionic acid methyl ester (0.35 mmol), and DMAP (0.01 g, 0.082 mmol) in CH2Cl2 (5 mL) is added EDCI (0.08 g, 0.42 mmol). After stirring for 2 h at RT, the mixture is concentrated. The residue is redissolved in EtOAc, and the organics are washed with 1N HCl (1×), 2N NaOH (2×), water, and brine, and dried with MgSO4. The crude material is purified by flash chromatography to yield the title compound.

Workup

  1. concentrationthe mixture is concentrated
  2. dissolutionThe residue is redissolved in EtOAc
  3. washthe organics are washed with 1N HCl (1×), 2N NaOH (2×), water, and brine
  4. dry with materialdried with MgSO4
  5. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-294d5b665167424b98630aca576ee115
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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