HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-(3-(Cyclopropylmethyl)ureido)-N-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-N-methylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-(3-(Cyclopropylmethyl)ureido)benzoic acid | HCID 58055819 | — |
| Reactant | 1,1,1,3,3,3-Hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-ol | HCID 86670959 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | 4-(3-(Cyclopropylmethyl)ureido)-N-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-N-methylbenzamide | HCID 86670961 | 77.9% |
Reaction Steps
To a mixture of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.810 mmol, 190 mg), 1,1,1,3,3,3-hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-ol (0.810 mmol, 300 mg) and triethylamine (1.944 mmol, 0.271 mL, 197 mg) in dichloromethane (50 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.972 mmol, 186 mg). The reaction was stirred for 24 hours. Chromatography on silica eluting with dichloromethane to dichloromethane/methanol (10%) gave the title compound (370 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09108939B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-fc1d828f8338496cac17239901602189 |
| Source note | uspto-grants-2015_08 |