HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylamine → (S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (S)-7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoic acid | HCID 90149568 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate | HCID 90149176 | — |
Reaction Steps
To a stirred solution of F5 in DMF (0.1 M) were added HATU (2.0 eq.) and DIPEA (3.0 eq.) followed after 10 min by methylamine (2.0 M solution in THF, 5.0 eq.). Reaction mixture was stirred at room temperature for 16 h. Then, reaction mixture was diluted with EtOAc, washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude was purified by column chromatography (eluent: Petroleum ether/EtOAc from 1:1 to 100% EtOAc, then EtOAc/MeOH=95:5) to give the title compound as pale yellow solid. MS (ES+) C29H32N4O5: 517 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365541B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-e38efdc0bf05487090e6c2cee57928b7 |
| Source note | uspto-grants-2016_06 |