HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → (5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| 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 | (5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid | HCID 90303981 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamide | HCID 90304213 | 46.2% |
Reaction Steps
To a solution of (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid (130 mg, 0.23 mmol) in DMF (2 mL) was added NH4Cl (37 mg, 0.69 mmol), TEA (93 mg, 0.92 mmol) and HATU (175 mg, 0.46 mmol). The mixture was stirred at RT overnight. After the reaction was completed, the solvent was evaporated and the residue was purified by Pre-TLC to give (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamide (60 mg, yield 46%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09446130B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-f938d3d6039346d2a668c4e697224bb7 |
| Source note | uspto-grants-2016_09 |