HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (S)-N-(3-hydroxy-5-(4-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-(3-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)methanesulfonamide | HCID 72219545 | — |
| Reactant | (S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one | HCID 131736160 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | (S)-N-(3-hydroxy-5-(4-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide | HCID 131736161 | 83.2% |
Reaction Steps
(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (160 mg, 0.28 mmol) was treated with N-(3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (220 mg, 0.70 mmol), sodium carbonate (86.3 mg, 0.81 mmols) and bis(triphenylphosphine)palladium(II) dichloride (81.8 mg, 0.1 mmol) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 80%, hexane-ethyl acetate) to give 160 mg (79% yield) of the title compound. Purity 94%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-221e6076d4ae421b9cca807f69f9cb7f |
| Source note | uspto-grants-2016_07 |