HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Isopropenyl chloroformate | HCID 93846 | — |
| Reactant | N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide | HCID 90410520 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | Prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate | HCID 131735228 | 94.2% |
Reaction Steps
A solution of N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide (0.280 g, 0.815 mmol) in pyridine (6 mL) was treated with isopropenyl chloroformate (0.100 mL, 0.913 mmol) and stirred at RT overnight. The mixture was treated with water and DCM, stirred for 0.5 h, the layers separated and the aqueous layer extracted with additional DCM (3×). The combined organics were dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (328 mg, 94%). MS (ESI) m/z: 428.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309224B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-2af0b87d70204ed78f6ec8cdb2f1b582 |
| Source note | uspto-grants-2016_04 |