HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → [4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-[5-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2774010 | — |
| Reactant | (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amine | HCID 59023119 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-dioxane N,N-dimethylformamide | HCID 21712069 | — |
| Product | Ammonia | HCID 222 | — |
| Product | [4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-[5-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine | HCID 59023024 | 72.6% |
Reaction Steps
In the same way as described for Compound 178, step 4, using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amine (49.4 mg, 0.133 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (51.6 mg, 0.266 mmol), Pd(PPh3)4 (39.3 mg, 0.034 mmol), 1.5 M Na2CO3 (0.710 mL, 1.07 mmol) in (2:1) DMF-dioxane (1.5 mL). Purification by Isolute FlashSilicaII cartridge chromatography eluting with 97:3 DCM:NH3 (7M in MeOH) affords the title compound as a white solid (17.3 mg, 36%). LCMS: Rt 2.60 min (96%), m/z 359 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 4.45 (3H, s), 7.72 (1H, s), 7.81 (1H, s), 8.05 (2H, d), 8.10 (1H, s), 8.21 (1H, s), 8.33 (2H, d), 8.48 (1H, s), 9.91 (1H, s), 13.42 (1H, br s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178530B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-ad7f0e6dd0d94060b65cba0f61dbaac2 |
| Source note | uspto-grants-2012_05 |