1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-{[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-amino}-2-methyl-phenyl)-propionic acid methyl ester

HRID 854566Notes

Reaction equation

HRID 854566 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:7][C:8]=1[C:9](O)=[O:10])([CH3:3])[CH3:2].[CH3:22][O:23][C:24](=[O:35])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][C:28]=1[CH3:34].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:22][O:23][C:24](=[O:35])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:9]([C:8]2[S:7][C:6]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=3)=[N:5][C:4]=2[CH:1]([CH3:3])[CH3:2])=[O:10])=[CH:29][C:28]=1[CH3:34]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoateHCID 589340934-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid

Product 1

HCID 694759173-(4-{[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-amino}-2-methyl-phenyl)-propionic acid methyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid (0.11 g, 0.35 mmol), 3-(4-Amino-2-methyl-phenyl)-propionic acid methyl ester (0.07 g, 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 (0.12 g, 70%).

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-661ee600e0c64ef3979cdbb62ca3d8ae
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

Loading…