HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl acetoacetate → 5-(2,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl acetoacetate | HCID 7757 | — |
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | 2,2-Dimethylcyclopropanecarboxamide | HCID 574717 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 1-(2,5-Bis-trifluoromethyl-phenyl)-2-bromo-ethanone | HCID 22137987 | — |
| Reactant | 1-(2,2-Dimethylcyclopropyl)methanamine | HCID 45791189 | — |
| Product | 5-(2,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide | HCID 58999024 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 68, using 3-oxo-butyric acid methyl ester as compound of formula R, 1-(2,5-bis-trifluoromethyl-phenyl)-2-bromo-ethanone as compound of formula S, C-(2,2-dimethyl-cyclopropyl)-methylamine (prepared from 2,2-dimethyl-cyclopropanecarboxylic acid amide by reduction with LiAlH4 according to the procedure described by Saski et al. J. Org. Chem. 1971, 36, 1968-1971) as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 501.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07294644B2 |
| Source dataset | uspto-grants-2007_11 |
| ORD ID | ord-39b733076291469c991d814aab88bc6f |
| Source note | uspto-grants-2007_11 |