Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-tert-Butyl-1,3-thiazol-2-amine | HCID 2734202 | — |
| Reactant | 4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid | HCID 58244395 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 86664395 | HCID 86664395 | 64.7% |
Reaction Steps
4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (53 mg, 0.141 mmol) and 2-amino-4-tert-butylthiazole (44.0 mg, 0.281 mmol) in DMA were treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53.9 mg, 0.281 mmol) followed by 1-hydroxy-7-azabenzotriazole (19.1 mg, 0.141 mmol) at ambient temperature. The reaction was heated to 50° C. for 14 hours. The reaction was diluted with ethyl acetate, washed with 1 N HCl, saturated aqueous bicarbonate, and brine. The ethyl acetate layer was dried with sodium sulfate and the product purified on SP1 (20 to 65% Ethyl acetate/hexane) to provide the desired compound (47 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08785445B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-21d4756bfd88447cba894a82fa8d7362 |
|---|
| Source note | uspto-grants-2014_07 |
|---|
