HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl acetoacetate → 5-(5-Chloro-2-fluoro-phenyl)-1-((S)-2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl acetoacetate | HCID 7757 | — |
| Reactant | (1R,2R)-2-Aminocyclohexanol | HCID 735777 | — |
| Reactant | (S)-2,2-Dimethylcyclopropanecarboxamide | HCID 10197657 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 2-Bromo-1-(5-chloro-2-fluorophenyl)ethanone | HCID 79021921 | — |
| Product | 5-(5-Chloro-2-fluoro-phenyl)-1-((S)-2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide | HCID 58998912 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 68, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-(5-chloro-2-fluoro-phenyl)-ethanone as compound of formula S, C—(S)-(2,2-dimethyl-cyclopropyl)-methylamine (prepared from (S)-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 (1R,2R)-2-amino-cyclohexanol as R1R2NH, MS (ISP) 433.4 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07579369B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-6496efb29bb34e8aac0a5e8ecf83f76c |
| Source note | uspto-grants-2009_08 |