HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → (S)-4-Hydroxy-N-(3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | (S)-4-Methoxy-N-(3-(4-((1-(5-methyl-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)benzenesulfonamide | HCID 131736186 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-4-Hydroxy-N-(3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)benzenesulfonamide | HCID 90102152 | 79% |
Reaction Steps
(S)-4-Methoxy-N-(3-(4-((1-(5-methyl-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)benzenesulfonamide (57 mg, 0.05 mmol) was treated with boron tribromide (1M in dichloromethane, 536 μL, 0.54 mmol) in dichloromethane (1.15 mL) and then with a solution of ammonia (7N in methanol, 1.15 ml, 6.05 mmol) according to the method described in Example 27. The residue was purified using SP1 ® Purification System (0% to 6% dichloromethane-2-propanol) to obtain 25 mg (72% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-c7b7980a1c8a442298af412c2d6f3129 |
| Source note | uspto-grants-2016_07 |