HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-(Cyclopropylmethyl)-3-(4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carbonyl)phenyl)urea
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 | 2-(4-((1,4-Diazepan-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol | HCID 86638561 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(Cyclopropylmethyl)-3-(4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carbonyl)phenyl)urea | HCID 86638562 | 63.8% |
Reaction Steps
To a mixture of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (2.134 mmol, 0.5 g), 2-(4-((1,4-diazepan-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (2.134 mmol, 0.761 g) and triethylamine (5.34 mmol, 0.744 mL, 0.540 g) in dichloromethane (30 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.56 mmol, 0.491 g). The reaction was stirred for 24 hours then was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (6%) then re-chromatographed on silica eluting with ethyl acetate to ethyl acetate/methanol (2%) to give the title compound (780 mg). MS (ESI) m/z 573.0 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08357679B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-d0ec0242bd444ff59d839c77978c650c |
| Source note | uspto-grants-2013_01 |