Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethoxyacetic acid | HCID 12301 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromothiazol-2-amine monohydrobromide | HCID 2723848 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22170710 | HCID 22170710 | 70.2% |
Reaction Steps
EDCI (0.53 g, 2.78 mmol) was added to a solution of ethoxyacetic acid (0.29 g, 2.78 mmol) in CH2Cl2 (5 ml) under ice-cooling. After stirring for 1 h, a solution of 2-amino-5-bromothiazole hydrobromide (0.60 g, 2.31 mmol) and diisopropylethylamine (0.40 ml, 2.34 mmol) in CH2Cl2 (5 ml) was added dropwise, and the entire mixture was kept at 0° C. for 1 h, then at room temperature overnight. The solution was evaporated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was further washed with water, 5% citric acid, water, saturated sodium bicarbonate, and water. Drying over sodium sulfate and evaporation gave a solid which was triturated with isopropyl ether to give the title compound as a beige solid (0.43 g; 70%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07037929B1 |
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| Source dataset | uspto-grants-2006_05 |
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| ORD ID | ord-8b129707d220460d9567528f7249942b |
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| Source note | uspto-grants-2006_05 |
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