HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,2,2-Trifluoroethanol → 2-(1-Methyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,2,2-Trifluoroethanol | HCID 6409 | — |
| 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 | Azetidine-3-carbonitrile hydrochloride | HCID 45072465 | — |
| Reactant | 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid | HCID 57829653 | — |
| Reactant | 2-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid | HCID 67008937 | — |
| Product | 2-(1-Methyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide | HCID 53386311 | — |
Reaction Steps
Prepared according to the procedure outlined in Example 1 substituting 3-cyanoazetidine hydrochloride for pyrrolidine, Boc-D-cyclopropyl glycine for Boc-D-tert-leucine, and 2-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid for 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid. N-Boc deprotection was achieved using 2,2,2-trifluoroethanol in a microwave reactor. MS: (M+H)+=405.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518945B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-78853117178346179aeb29d77a6dff33 |
| Source note | uspto-grants-2013_08 |