Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| 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 | HCID 178522847 | HCID 178522847 | — |
| Reactant | HCID 178524246 | HCID 178524246 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178522832 | HCID 178522832 | — |
Reaction Steps
2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 2-fluoro-benzylamide was synthesized from 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid, benzylamine, DIEA, HATU and DMF using a similar procedure as 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 3-fluoro-benzylamide yielding 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 2-fluoro-benzylamide. LC/MS calcd for C28H23ClFN5O2 (m/e) 515.0, obsd 516 (M+H). 1H NMR (tautomers, DMSO-d6) δ: 13.33-13.49 (m, 1H), 11.14-11.45 (m, 1H), 10.05-10.92 (m, 1H), 9.08-9.32 (m, 1H), 7.70-7.98 (m, 2H), 7.02-7.61 (m, 11H), 6.16-6.32 (m, 1H), 4.53-4.80 (m, 2H), 3.43-3.84 (m, 2H), 2.75-3.12 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09334480B2 |
|---|
| Source dataset | uspto-grants-2016_05 |
|---|
| ORD ID | ord-7fd2590c785147be9ba6f1832d6a725f |
|---|
| Source note | uspto-grants-2016_05 |
|---|
