HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 6-[({1-[2-(6-Methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde | HCID 21873737 | — |
| Reactant | Sodiumacetoxyborohydride | HCID 23670382 | — |
| Reactant | 4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one | HCID 57815394 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-[({1-[2-(6-Methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one | HCID 57928127 | 28.8% |
Reaction Steps
4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (Intermediate 202, 0.125 g) was reacted with 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (50 mg) and sodium acetoxyborohydride (110 mg) as described for Example 107. Chromatography on silica gel with 0-20% methanol in dichloromethane and trituration of the product from ether gave 37.6 mg of the title compound as acetic acid salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08124602B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-2d051b19f62640edbdf620a02ebefca6 |
| Source note | uspto-grants-2012_02 |