HuagongsheHuagongshe Chemistry Print Report · For research reference only
Azetidine → 2-[2-(Azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Azetidine | HCID 10422 | — |
| 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 | [4-(Benzyloxy)-2-cyanophenyl]acetic acid | HCID 70818555 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[2-(Azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile | HCID 70818634 | — |
Reaction Steps
[4-(Benzyloxy)-2-cyanophenyl]acetic acid (0.40 g, 1.50 mmol) was dissolved in DMF (5 ml) and azetidine (0.128 g, 2.25 mmol), DIEA (0.78 ml, 4.49 mmol), and HATU (1.14 g, 2.99 mmol) added. The mixture was stirred at RT for 1 hr. The solution was loaded directly onto a Biotage RP C18 cartridge (30 g) and purified using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. The volatiles were removed in vacuo to afford the title compound. LC/MS (m/z): 307 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018224B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-b5892d823fa64ae59295985c81951146 |
| Source note | uspto-grants-2015_04 |