Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isobutyric Acid | HCID 6590 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| 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 68677071 | HCID 68677071 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58728645 | HCID 58728645 | 72% |
Reaction Steps
A mixture of 1-(8-{2-[4-(1,3-benzodioxol-5-yl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole dihydrochloride (0.20 g, 0.39 mmol), triethylamine (0.17 mL, 1.25 mmol) and isobutyric acid (34 mg, 0.39 mmol) in dimethylformamide (1.25 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (163 mg, 0.43 mmol) and the resulting mixture was stirred for 1 h at rt. The mixture was diluted with water and the resulting precipitate was collected, washed with saturated sodium bicarbonate solution, with water and dried to give 1-((1R,5S)-8-{2-[4-(1,3-benzodioxol-5-yl)-1-isobutyrylpiperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole as a solid (0.15 g, 72%). HRMS C33H42N4O3 m/z 543.3335 (M+H)Cal. 543.3322 (M+H)Obs..
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07645771B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-381217ea995c4288b56655d6b7bcc97e |
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| Source note | uspto-grants-2010_01 |
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