HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Encenicline enantiomer
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | 7-Chloro-1-benzothiophene-2-carboxylic acid | HCID 10198242 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Encenicline enantiomer | HCID 68431081 | — |
Reaction Steps
176.2 mg (0.83 mmol) of 7-chloro-1-benzothiophene-2-carboxylic acid, 150 mg (0.75 mmol) of S-3-aminoquinuclidine dihydrochloride, 343.7 mg (0.90 mmol) of HATU, 350.5 mg (2.71 mmol) of N,N-diisopropylethylamine and 3.0 ml of DMF are reacted according to the general procedure (variant B). The reaction mixture is purified by preparative HPLC. The product is dissolved in a mixture of 4M HCl in dioxane and methanol and then concentrated. 231.9 mg (85.7% of theory) of the title compound are obtained. The analytical data correspond to those of the enantiomeric compound from example 69.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08884017B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-e5cd8f77bd804c99bdc08f8b077fc880 |
| Source note | uspto-grants-2014_11 |