HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1'-Carbonyldiimidazole → HCID 58386328, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Reactant | (R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine | HCID 67330818 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58386328 | HCID 58386328 | 83.6% |
Reaction Steps
To a DCM (5 mL) solution of (R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (25 mg, 0.076 mmol) and DIEA (0.04 mL, 0.23 mmol) was added CDI (25 mg, 0.15 mmol) at ambient temperature in one portion. After stirring for one hour, (S)-pyrrolidin-3-ol (20 mg, 0.23 mmol) was added in one portion. The reaction was stirred overnight before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 60% acetonitrile/water to yield the final product as a yellowish solid (28 mg, 83% yield). MS (apci) m/z=441.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447104B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-8362727315a74bd8a8f80f5d4b0a36c0 |
| Source note | uspto-grants-2016_09 |