HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isobutyl chloroformate → {4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | 1-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]- | HCID 16071550 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | {4-[5-(4-Fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidin-2-yl}carbamic acid isobutyl ester | HCID 23652795 | — |
Reaction Steps
110 μl (0.84 mMol) isobutyl chloroformate are added portionwise to a solution of 300 mg (0.68 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (Step 10.3) in 4.5 ml CH2Cl2 and 7.5 ml pyridine. After 1 h, the solution is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2-CH2Cl2/EtOH 19:1) gives the title compound: MS: [M+1]+=543.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08133886B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-3f2524e1b6d84e93a9a3fb39d57362f6 |
| Source note | uspto-grants-2012_03 |