HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-((S)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 2,2,2-Trifluoroethanol | HCID 6409 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | (2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid | HCID 7005057 | — |
| Reactant | (R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid | HCID 7146275 | — |
| Reactant | HCID 34180561 | HCID 34180561 | — |
| Product | 2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-((S)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide | HCID 53386418 | — |
Reaction Steps
Prepared according to the procedure outlined in Example 1 substituting (S)-pyrrolidine-3-carbonitrile for pyrrolidine and Boc-D-cyclopropyl glycine for Boc-D-tert-leucine. N-Boc deprotection in step 2 was achieved using 2,2,2-trifluoroethanol in a microwave reactor. SEM deprotection in step 4 was achieved using CsF in refluxing acetonitrile. MS: (M+H)+=379.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518945B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-0a3d21303b1b4958b45b0a946e544e3e |
| Source note | uspto-grants-2013_08 |