HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Chloro-4-fluoroaniline → 2-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Chloro-4-fluoroaniline | HCID 9708 | — |
| Reactant | Methanesulfonic anhydride | HCID 81560 | — |
| Reactant | 1,3-Dimethyl-1H-pyrazol-5-amine | HCID 520721 | — |
| Reactant | 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester | HCID 86703101 | — |
| Reactant | 5-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester | HCID 86703158 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 2-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one | HCID 86703157 | — |
Reaction Steps
The title compound was prepared in analogy to the procedure described for Intermediate D but in the step corresponding to Step D2, 2,5-dimethyl-2H-pyrazol-3-ylamine [3524-32-1] and 5-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BI1) were used instead of 3-chloro-4-fluoroaniline and 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester respectively. Moreover, in this step, the procedure described for Step L3 using Ms2O and Et3N was used. The title compound (containing some of the corresponding 2-chloro analog) was obtained as a solid. ESI-MS: tR=1.14 min, [M+H]+ 465/467/469 (LC-MS 1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365576B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-8455e3d55da34de0a0633a68dfb4c05d |
| Source note | uspto-grants-2016_06 |