HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester | HCID 67398032 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochloride | HCID 67398841 | 102% |
Reaction Steps
2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (145 mg) obtained in Example 242-3 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=20:1). The obtained compound was dissolved in diethyl ether (4 mL), 4 mol/L hydrochloric acid-ethyl acetate (0.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration to give the title compound (69 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08026370B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-a24a98fa14144d23b00a56d2ee93f354 |
| Source note | uspto-grants-2011_09 |