HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (S)-2-((S)-3,3-Dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-7-((3R,5S)-1-((S)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-N-((S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (S)-N-((R)-Chroman-4-yl)-2-((S)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-7-((3R,5S)-1-((S)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide | HCID 86705911 | — |
| Reactant | (S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-phenylethanamine | HCID 86705913 | — |
| Product | (S)-2-((S)-3,3-Dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-7-((3R,5S)-1-((S)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-N-((S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide | HCID 86705912 | 33% |
Reaction Steps
Following procedures analogous to those described for the preparation of Example 33, (S)-2-(tert-butoxycarbonyl)-7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Compound F of Example 33, 60 mg, 0.10 mmol) and (S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-phenylethanamine, TFA (31 mg, 0.10 mmol) were converted to the title compound (34 mg, 33% over 6 steps). MS (ESI+) m/z 1001.7 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889712B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-5651c19afe0843758c979639aa35762b |
| Source note | uspto-grants-2014_11 |