HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Chloropyrazinoic acid | HCID 465472 | — |
| Reactant | (S)-1-Cyclopropylethylamine | HCID 7363995 | — |
| 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 | Dichloromethane | HCID 6344 | — |
| Product | 5-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamide | HCID 86675759 | 79.8% |
Reaction Steps
A mixture of 5-chloropyrazine-2-carboxylic acid (0.5 g, 3 mmol), (1S)-1-cyclopropylethanamine (0.30 g, 3.5 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.8 g, 4.7 mmol) and N,N-diisopropylethylamine (1.6 mL, 9.5 mmol) in methylene chloride (5 mL) was stirred at room temperature overnight (22 h.). The mixture was concentrated under reduced pressure. The residue was was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%) to afford the desired product (0.54 g). LCMS (M+H)+: m/z=226.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691807B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-c075b0a390494c879de2b9cecdefda5f |
| Source note | uspto-grants-2014_04 |