HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-chloro-N2-(2,3-dimethyl-2H-indazol-6-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | tert-butyl 5-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate | HCID 118390172 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-chloro-N2-(2,3-dimethyl-2H-indazol-6-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine | HCID 118390163 | 49.7% |
Reaction Steps
To a solution of tert-butyl 5-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (452.1 mg, 0.908 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (10 mL, 40 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was dissolved in water (30 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (250 mL×3). The combined organic phases were washed with brine (250 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/5) to give the title compound as a beige solid (179.6 mg, 49.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09399637B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-24b9f4041f3f489eb3a25caf78f5afee |
| Source note | uspto-grants-2016_07 |