HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204291Generated: November 1, 2026
4-Methylmorpholine → 5-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one
https://huagongshe.com/reaction/2204291
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-[(3-chloro-2-fluoro-phenylamino)-(4-chloro-2-methyl-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid | HCID 86703094 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one | HCID 86703093 | — |
Reaction Steps
A mixture of 2-[(3-chloro-2-fluoro-phenylamino)-(4-chloro-2-methyl-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid (Step A2) (2.257 mmol), HATU (2.482 mmol) and NMM (6.77 mmol) in DMF (30 mL) was heated at 80° C. for 18 h. After cooling to rt, the reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. tR: 5.31 min (HPLC 1); ESI-MS: tR=1.29 min, [M+H]+ 417/419 (LC-MS 1); TLC: Rf=0.13 (1:3 EtOAc/heptanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365576B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-f87116c44487467e8ddeae655ebed326 |
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| Source note | uspto-grants-2016_06 |
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