HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (RS)-1-[2-(4,5-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | (RS)-4,5-Difluoro-2-piperidin-2-ylmethyl-1H-benzoimidazole | HCID 17973676 | — |
| Reactant | 5-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid | HCID 22324125 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (RS)-1-[2-(4,5-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone | HCID 17973673 | 85% |
Reaction Steps
A solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (1.00 g, 4.2 mmol), HATU (1.60 g, 4.2 mmol) and N,N-diisopropylethylamine (2.00 ml, 11.6 mmol) in DMF (20 ml) was stirred at room temperature under argon for 2 min. The mixture was then treated with (RS)-4,5-difluoro-2-piperidin-2-ylmethyl-1H-benzoimidazole, D21 (1.06 g, 4.2 mmol) and stirring was continued for 16 h. The solvent was removed in vacuo and the residue was washed with water then was triturated with ethyl acetate to afford the title compound as an off-white solid (1.68 g, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07897618B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-fa5a154456fa4444ab9f802153653a81 |
| Source note | uspto-grants-2011_03 |