HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-({[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-carbamoyl}-methyl)-2-methoxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Methoxybenzoic acid | HCID 11370 | — |
| 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 | 2-Amino-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide | HCID 68714368 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Chloroform methanol | HCID 21584188 | — |
| Product | N-({[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-carbamoyl}-methyl)-2-methoxy-benzamide | HCID 11676451 | — |
Reaction Steps
A solution of 2-methoxybenzoic acid in dimethylformamide is treated with triethylamine (2 M equivalents) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (1 M equivalent). To the reaction mixture is added a solution of 2-Amino-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide (1 M equivalent) in dimethylformamide and left to stir for 1.5 hours. The reaction mixture is diluted with chloroform/methanol 50:50 and applied to a SCX-3 1 g cartridge. The cartridge is washed with chloroform/methanol 50:50, and the compound eluted with a solution of 10% ammonia in methanol. The solvent is evaporated to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691841B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-5805088657494b81b8f569c57f9b0107 |
| Source note | uspto-grants-2010_04 |