HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-methyl-2-pyrrolidone → 2-(4-Methylpyridin-3-yl)-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyridine | HCID 92342 | — |
| Reactant | Ethyl 3-(2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-3-carboxylate trihydrochloride | HCID 66722530 | — |
| Product | 2-(4-Methylpyridin-3-yl)-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one | HCID 57971043 | — |
Reaction Steps
A mixture of ethyl 3-{2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-3-carboxylate trihydrochloride (42.8 mg, 0.000107 mol), 2-chloro-5-(trifluoromethyl)pyridine (23 mg, 0.00013 mol) and N,N-diisopropylethylamine (0.056 mL, 0.00032 mol) in N-methylpyrrolidinone (0.8 mL, 0.008 mol) was irradiated with microwaves to 180° C. for 20 min. Sodium hydride (30.0 mg) was then added to the above solution and the mixture was stirred overnight. The product was purified by prep-HPLC. LC-MS: 391.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08563570B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-d03877cc35a545de813e5301e5ea6154 |
| Source note | uspto-grants-2013_10 |