HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | 4-((8-((5-Cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide | HCID 118036870 | — |
| Product | (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide | HCID 118036487 | — |
Reaction Steps
A solution of 4-((8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide (Example 222, 5 mg, 0.01 mmol) in DMSO (1 ml) was stirred at room temperature. After 30 h, the reaction mixture was concentrated and the residue purified by reverse phase chromatography: Atlantis C18 T3 column (3.5 um, 4.6×150 mm, 45° C.), eluting with 1:1 acetonitrile/water (containing 10 mM NH4OAc, 0.02% TFA). The product containing fraction was evaporated to give the title compound as a gray solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266883B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-bf8bb4eb53fe4a99856be9fdb2fa355f |
| Source note | uspto-grants-2016_02 |