HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → [5-tert-Butyl-2-(3-morpholin-4-yl-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,2,2-Trichloroethyl chloroformate | HCID 87063 | — |
| Reactant | HCID 86686708 | HCID 86686708 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [5-tert-Butyl-2-(3-morpholin-4-yl-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester | HCID 86686709 | 46.7% |
Reaction Steps
2,2,2-Trichloroethylchloroformate (175 mg, 0.82 mmol) was added dropwise to a solution of Intermediate 23d (190 mg, 0.63 mmol) and DIPEA (244 mg, 1.89 mmol) in THF (10 mL), and the mixture stirred at RT for 1.5 h. The mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (140 mg, 46%). LCMS (Method 4): Rt 3.94, m/z 475 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835431B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-7447b043c21849b1bac8cc0797da5bd1 |
| Source note | uspto-grants-2014_09 |