HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-Methyl 6-(1-amino-4-methyl-1-oxopentan-2-ylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | (R)-2-Amino-4-methylpentanamide | HCID 7271815 | — |
| Reactant | methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate | HCID 58317582 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | (R)-Methyl 6-(1-amino-4-methyl-1-oxopentan-2-ylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate | HCID 67237475 | 11% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A mixture of methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate (82.9 mg, 0.300 mmol) and (R)-2-amino-4-methylpentanamide (39.0 mg, 0.300 mmol) in DMA (2 mL) was stirred at 150° C. for 12 h. Water was subsequently added and the mixture was extracted with EtOAc. The organic layers were washed with saturated aq NaHCO3, water, and brine, were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, EtOAc) to give the title compound as a yellow oil (11.7 mg, 11%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08440689B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-a01c30d4233d4913bfb3ef880ba92774 |
| Source note | uspto-grants-2013_05 |