HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-((R)-1-chloro-ethyl)-isonicotinonitrile → 2-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}isonicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-((R)-1-chloro-ethyl)-isonicotinonitrile | HCID 59868840 | — |
| Reactant | HCID 178445911 | HCID 178445911 | — |
| Product | 2-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}isonicotinonitrile | HCID 59186882 | 20.2% |
Reaction Steps
The title compound was prepared according to General Method A starting from 2-((R)-1-chloro-ethyl)-isonicotinonitrile (46 mg, 0.28 mmol) and (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (69 mg, 0.23 mmol). Purification by chiral HPLC (Column: Chiralpak AD 50×150 mm, eluent: heptane:isopropanol 85:15), flowrate 60 ml/min) yielded the title compound (20 mg, 20% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158785B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-3aea12f660ae42a595950e40397af94a |
| Source note | uspto-grants-2012_04 |