HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole-3-Acetic Acid → 2-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole-3-Acetic Acid | HCID 802 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 86656618 | HCID 86656618 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide | HCID 86656589 | 57.4% |
Reaction Steps
200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 140 mg Indolyl-3-acetic acid, 98 mg HOBT and 0.6 ml Et3N are dissolved in 8 ml DMF. To this mixture are added 278 mg EDC and the mixture is stirred overnight. The reaction mixture is evaporated and the crude product is purified by silica gel flash chromatography. 180 mg of the title compound are obtained in 57% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575193B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-f57a3c05b9b846639344716c699c34cb |
| Source note | uspto-grants-2013_11 |