HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(6-Methoxy-pyridine-2-carbonyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Methoxypicolinic acid | HCID 570891 | — |
| Reactant | 1-Chloro-N,N-2-trimethylpropenylamine | HCID 640792 | — |
| Reactant | 1-Boc-3,3-dimethylpiperazine | HCID 22710387 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 4-(6-Methoxy-pyridine-2-carbonyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester | HCID 86688301 | — |
Reaction Steps
A mixture of 410 mg (2.28 mmol) 6-methoxy-2-pyridinecarboxylic acid and 400 μL (3.02 mmol) 1-chloro-N,N,2-trimethylpropenylamine in 10 mL THF was stirred at RT. After 1.5 h, 600 mg (2.66 mmol) 3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester and 1.00 mL (5.81 mmol) DIPEA was added and the reaction mixture was stirred at RT for 30 min. The reaction mixture was diluted with saturated NaHCO3 solution and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=1/1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883789B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-260674243acf4dd5bc9d09582171236f |
| Source note | uspto-grants-2014_11 |