HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 68995468, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde | HCID 21873668 | — |
| Reactant | HCID 68810511 | HCID 68810511 | — |
| Product | HCID 68995468 | HCID 68995468 | 48% |
Reaction Steps
1-[2-(4-amino-1-piperidinyl)ethyl]-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one (0.056 g, 0.184 mmol) and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (0.030 g, 0.184 mmol) was dissolved in CHCl3 (1 ml) and MeOH (0.1 ml) at rt under argon. NaBH(OAc)3 (0.117 g, 0.552 mmol) was then added and the reaction was allowed to stir at rt for 16 h. After which it was purified by chromatography on silica gel (10 g) using a 0-30% MeOH in DCM gradient to give the free base of the title compound as a yellow oil (0.041 g, 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-491c5e575b9147d18699e30b5a736b6e |
| Source note | uspto-grants-2011_12 |