HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-[(4-Isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl N-{4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridyl}carbamate | HCID 22063558 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[(4-Isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinamine | HCID 22063780 | 66% |
Reaction Steps
tert-Butyl N-{4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridyl}carbamate (706 mg, 2.202 mmol) dissolved in dichloromethane (20 ml) was added dropwise with trifluoroacetic acid (20 ml) under ice cooling, then warmed to room temperature and stirred for 2 hours. The reaction solution was concentrated under reduced pressure, diluted with chloroform, then neutralized with saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=50:1→30:1→20:1) to obtain 331 mg (66%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07056917B2 |
| Source dataset | uspto-grants-2006_06 |
| ORD ID | ord-917ab836a7fd40a9810ae5e8378dab03 |
| Source note | uspto-grants-2006_06 |