HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)-1-(1-Phenylpropyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Quinolin-5-ylboronic acid | HCID 5153389 | — |
| Reactant | (S)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine | HCID 68853527 | — |
| Reactant | (S)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine | HCID 86626385 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-1-(1-Phenylpropyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one | HCID 66699761 | 77% |
Reaction Steps
(S)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (S)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine (0.560 g, 1.83 mmol), quinoline-5-boronic acid (0.348 g, 2.01 mmol), tetrakis(triphenylphosphine)palladium (0.211 g, 0.183 mmol), potassium carbonate (1.01 g, 7.32 mmol), water (8 mL) and dimethylformamide (30 mL) were reacted according to General Procedure B. The crude was purified via Biotage silica gel chromatography (0-10% methanol/dichloromethane, 40S column) to afford the title compound (0.500 g, 77% yield). MS (ESI) m/z 356.3 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08372976B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-d0fb5b24e51f4269b9778b3a46eba73c |
| Source note | uspto-grants-2013_02 |