HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(1-Pyrrolidinyl)piperidine | HCID 78703 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid | HCID 67133239 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone | HCID 57541122 | 90.1% |
Reaction Steps
7.20 g (17.5 mmol) of 2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid (intermediate 1) were dissolved in 290 ml of DMF and treated with 6.846 g (17.5 mmol) of HATU. 7.30 ml=5.30 g (52.4 mmol) of Et3N were added and after 30 min, a solution of 2.72 g (17.5 mmol) of 4-pyrrolidin-1-yl-piperidine in 70 ml of DMF was added. After 16 hours, the reaction mixture was poured into crashed ice and extracted three times with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 8.65 g (90%) of the title compound as light brown foam. MS: 549.3 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07935707B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-bbb307447e9f4f87b0ff0bca969427a0 |
| Source note | uspto-grants-2011_05 |