HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Methyl 3-(4-amino-2-methylphenyl)propanoate | HCID 54187007 | — |
| Reactant | 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid | HCID 58934093 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(4-{[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-amino}-2-methyl-phenyl)-propionic acid methyl ester | HCID 69475917 | 70% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07259175B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-661ee600e0c64ef3979cdbb62ca3d8ae |
| Source note | uspto-grants-2007_08 |