HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic anhydride → [4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diisopropyl-lambda4-sulfane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | Isopropyl sulfoxide | HCID 16645 | — |
| Reactant | 4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine | HCID 90010064 | — |
| Solvent | Ammonia | HCID 222 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | [4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]imino-diisopropyl-lambda4-sulfane | HCID 117966763 | 8% |
Reaction Steps
To a solution of diisopropyl sulfoxide (0.75 g, 5.6 mmo) in dichloromethane at −60° C. under argon was added dropwise trifluoroacetic anhydride (1.18 g, 5.6 mmol). The solution was stirred for 20 min at this temperature. Then the 4-(7-chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine (0.97 g, 2.5 mmol) was added and the solution stirred at −60° C. for 1 h. The reaction was diluted with aqueous ammonia; the organic layer separated and further washed with water and then dried and concentrated. The residue was re-crystallized with a mixture of ethyl acetate and petrole ether to give the title compound (80 mg; 8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09174967B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-13a3deb56a6846cb8d3139178c491fdf |
| Source note | uspto-grants-2015_11 |