HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → [5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (2-Methoxypyridin-4-yl)boronic acid | HCID 23546919 | — |
| Reactant | (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine | HCID 57590000 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-dioxane N,N-dimethylformamide | HCID 21712069 | — |
| Product | [5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine | HCID 57590084 | 47% |
Reaction Steps
This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (80 mg, 0.206 mmol), 2-methoxypyridine-4-boronic acid (63 mg, 0.412 mmol), Pd(PPh3)4 (0.052 mmol) and 1.5N Na2CO3 (1.1 mL, 1.65 mmol) in 2:1 DMF/dioxane (2.2 mL). The crude product is purified by silica gel column chromatography using 96:4 DCM:NH3 (7M in MeOH) and the fractions containing the desired product are combined and evaporated to afford the title compound (40 mg, 47%). HPLC (254 nm): Rt 2.26 min (65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07501411B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-36290199d22b4ef481537591340ea0ba |
| Source note | uspto-grants-2009_03 |