HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → (S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Chloro-5-iodopyrimidin-4-amine | HCID 46855833 | — |
| Reactant | (S)-2-(1-Amino-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrile | HCID 118433824 | — |
| Product | (S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrile | HCID 90103340 | 16% |
Reaction Steps
(S)-2-(1-Amino-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrile (51 mg, 0.12 mmol) was treated with 6-chloro-5-iodopyrimidin-4-amine (50 mg, 0.2 mmol), cesium fluoride (55 mg, 0.36 mmol) and N,N-diisopropylethylamine (170 μl, 0.98 mmol) according to the method of Preparation 13. The residue was purified by reverse phase using SP1® Purification System to give 12 mg (16% 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-1fe124d5de0042ec8a48f2e0a5f16b9e |
| Source note | uspto-grants-2016_07 |