HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanemethanamine → 1-(Cyclopropylmethyl)-3-(3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-ylsulfonyl)phenyl)urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | 4-Nitrophenyl chloroformate | HCID 82129 | — |
| Reactant | 2-(4-((4-(3-Aminophenylsulfonyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol | HCID 86638588 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | 1-(Cyclopropylmethyl)-3-(3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-ylsulfonyl)phenyl)urea | HCID 59175904 | 29.1% |
Reaction Steps
2-(4-((4-(3-Aminophenylsulfonyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.302 mmol, 150 mg) and 4-nitrophenyl carbonochloridate (0.302 mmol, 60.8 mg) were combined in a mixture of dichloromethane/dimethylformamide and stirred at room temperature for 1 hour. Cyclopropylmethanamine (0.603 mmol, 42.9 mg) was added and the reaction mixture was left to stir at room temperature for 15 minutes. The reaction mixture was purified by SCX chromatography and concentrated under vacuum. The residue was purified by silica column chromatography, eluting with 0%-4% methanol/dichloromethane gradient, to afford the title compound (52.3 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08357679B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-6a1ea11b08684ee8927e94d96fa3b685 |
| Source note | uspto-grants-2013_01 |