HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (s)-1-Allyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Chloro-1H-indole-2-carboxylic acid | HCID 82693 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (S)-1-allyl-3-amino-3,4-dihydrocarbostyril hydrochloride | HCID 69195858 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (s)-1-Allyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril | HCID 69195207 | 53.7% |
Reaction Steps
(S)-1-allyl-3-amino-3,4-dihydrocarbostyril hydrochloride (7.6 mg) was added to a mixture of tetrahydrofuran (4 mL), 5-chloroindole-2-carboxylic acid (6.9 mg), 1-hydroxy-7-azabenzotriazole (5.5 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.7 mg) at room temperature. Diisopropylethylamine (12 mg) was added, and the resulting yellow suspension was stirred under argon for 16 h, during which a solution formed. The solution was evaporated under vacuum and the residue was directly purified by reverse phase preparative HPLC to provide the title compound (6.5 mg). HPLC/MS [M+H]+, 380; HPLC/MS [M+Na]+, 402.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07098235B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-516d5b56df98453cafe3dd8cb1f58999 |
| Source note | uspto-grants-2006_08 |