HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 15333Generated: October 25, 2026
8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde → Racemic methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-[(cis)-3-fluoro-4-({[(phenylmethyl)oxy]carbonyl}amino)-1-piperidinyl]propanoate
https://huagongshe.com/reaction/15333
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde | HCID 16637176 | — |
| Reactant | Furo[2,3-c]pyridin-5-ylmethanol | HCID 22047174 | — |
| Reactant | HCID 57486873 | HCID 57486873 | — |
| Reactant | benzyl N-[(3R,4S)-3-fluoropiperidin-4-yl]carbamate | HCID 68566554 | — |
| Catalyst | 1,1,3,3-Tetramethylguanidine | HCID 66460 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Racemic methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-[(cis)-3-fluoro-4-({[(phenylmethyl)oxy]carbonyl}amino)-1-piperidinyl]propanoate | HCID 68685415 | 100% |
Reaction Steps
A solution of methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate (953 mg, 3.63 mmol), cis-phenylmethyl[3-fluoro-4-piperidinyl]carbamate Enantiomer 2 (for a synthesis see WO2004058144, prepared by analogy to Examples 142(b), (c) and (d) from the Enantiomer 2 of Example 142(a)) (1.1 g, 4.35 mmol) and 1,1,3,3-tetramethylguanidine (6 drops) in DMF (3.5 ml) was heated at 80° C. under argon for 3 hours, cooled and evaporated. Chromatography, eluting with 1% methanol/dichloromethane, gave the product in 100% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07732461B2 |
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| Source dataset | uspto-grants-2010_06 |
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| ORD ID | ord-721d8cceaacc48fea2c0ccf5e6db4a4c |
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| Source note | uspto-grants-2010_06 |
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