HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nipecotic Acid → 3-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nipecotic Acid | HCID 4498 | — |
| 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 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane | HCID 163938 | — |
Reaction Steps
A solution of the appropriate piperidine-3-carboxylic acid in dimethylformamide (10-20 ml/mmol) is admixed under argon at RT with HATU (1.2 eq.), N,N-diisopropylethylamine (2.2 eq.) and the appropriate alkyl N′-hydroxyimidocarbamate (1.1 eq.). The reaction mixture is stirred at RT until the formation of the intermediate is complete and then stirred further at 120° C. until the desired product is formed from this intermediate. The reaction mixture is then purified by means of preparative HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084469B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-f341009dd86d4fdd93b6ed168bbae2dc |
| Source note | uspto-grants-2011_12 |