HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 123825481, compound → HCID 118131051, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 123825481 | HCID 123825481 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 118131051 | HCID 118131051 | 66% |
Reaction Steps
3-(1-(4-amino-3-(3-((tert-butyldimethylsilyl)oxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one single enantiomer (intermediate R2, first eluted enantiomer under the conditions described above, 0.084 g, 0.13 mmol) was dissolved in a solution of 1M HCl in EtOH (0.416 ml) and the mixture was stirred at RT overnight. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel cartridge (DCM to DCM:MeOH=95:5) to afford title compound as a pale blue solid (0.043 g, 0.086 mmol, 66%). This compound proved to be the first eluted enantiomer under Chiral HPLC conditions of Method A7: Rt=16.0 min, ee>99%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321776B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-da14c3b635b74712a7b674d36f57ecc2 |
| Source note | uspto-grants-2016_04 |