HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → N-[(7-cyanoimidazo[1,2-a]pyridine-2-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 2,4,6-Tris((dimethylamino)methyl)phenol | HCID 7026 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid | HCID 53402578 | — |
| Reactant | 2-{[(1,3-Dioxolan-2-ylmethyl)-amino]-methyl}imidazo[1,2-a]pyridine-7-carbonitrile | HCID 67134825 | — |
| Product | N-[(7-cyanoimidazo[1,2-a]pyridine-2-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide | HCID 58024818 | 53.4% |
Reaction Steps
To a DMF 3 mL solution of product obtained in step A (410 mg, 1.58 mmol) were added 4-(2,4,6-trifluoro-benzoyl)-1H-pyrrole-2-carboxylic acid (427 mg, 1.58 mmol), EDC (396 mg, 2.06 mmol), HOBt (316 mg, 2.06 mmol) and triethylamine (0.443 mL, 3.17 mmol). The reaction mixture was stirred overnight at room temperature. The resulting suspension was filtered and diluted with EtOAc, washed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as foam (430 mg). LC/MS: m/z 510(M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08017605B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-1231c85ee821471c97104e3856bc062e |
| Source note | uspto-grants-2011_09 |