Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cysteamine | HCID 6058 | — |
| Reactant | HCID 20816871 | HCID 20816871 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22346432 | HCID 22346432 | — |
Reaction Steps
A mixture of methyl (2E)-3-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]-naphthyridin-5-yl)-2-propenoate (Example 137, Step 1) (1.22 g, 3.20 mmol) and cysteamine (4.0 g) in DMF (15 mL) was heated in an oil bath at 80° C. under an atmosphere of nitrogen with stirring for 18 hours. The product mixture was treated with water and the mixture was acidified to pH 2. The resultant precipitate was filtered, dissolved in DMSO, and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06921759B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-78caed494bd74b35a49460b2ee7f7d7d |
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| Source note | uspto-grants-2005_07 |
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