HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropylamine → 1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-isopropylurea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | (4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone | HCID 86638550 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-isopropylurea | HCID 59175851 | 46% |
Reaction Steps
(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-benzyl)piperazin-1-yl)methanone (0.209 mmol, 0.1 g) and N,N-diisopropylethylamine (0.709 mmol, 0.117 mL, 0.092 g) were stirred in dichloromethane at room temperature. Triphosgene (0.077 mmol, 0.023 g) was added and the reaction mixture stirred for 30 minutes. Isopropylamine (0.417 mmol, 0.036 mL, 0.025 g) was added and the reaction stirred for a further 30 minutes. The reaction was concentrated at reduced pressure and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane) to afford the title compound (20 mg). MS (ESI) m/z 565.5 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08357679B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-8870325c031e4316a15a281cdc2cbc95 |
| Source note | uspto-grants-2013_01 |