HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 86711679, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | 1H-pyrazole-1-acetic acid, 4-iodo- | HCID 19576647 | — |
| Reactant | 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine | HCID 67984610 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86711679 | HCID 86711679 | 100% |
Reaction Steps
To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.400 g, 1.83 mmol), 2-(4-iodo-pyrazol-1-yl)acetic acid (0.554 g, 2.2 mmol) and NEt3 (0.642 mL, 4.59 mmol) in DMF (5 mL) was added HATU (0.836 g, 2.2 mmol). The mixture was stirred at rt for 40 min. It was then quenched with water. The mixture was partitioned between EtOAc (100 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (SiO2, with a gradient elution of 0˜30% EtOAc/CH2Cl2) to yield 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-(4-iodopyrazol-1-yl)ethanone (0.82 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181241B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-9c62d5aeb1a743e684952479da46c1d4 |
| Source note | uspto-grants-2015_11 |