HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Aminothiazole → 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Aminothiazole | HCID 2155 | — |
| 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 | 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid | HCID 86653784 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide | HCID 86653785 | 52% |
Reaction Steps
2-(6-Chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid (6; 340 mg, 1.24 mmol) was taken up in DMF (5 mL) along with thiazol-2-amine (4; 125 mg, 1.24 mmol) and HATU (943 mg, 2.48 mmol). DIEA (0.41 mL, 2.48 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and the resulting solids were collected by filtration. Purification by silica gel chromatography (pentane/EtOAc) afforded 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide 7 as a pale yellow solid (215 mg, yield: 52%). MS (ESI) calcd for C16H10ClN5OS: 355.03; found: 356 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846947B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-d487be58354c464eb8014a8fed85fbe5 |
| Source note | uspto-grants-2014_09 |