Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Resmetirom | HCID 15981237 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 25230624 | HCID 25230624 | 92.1% |
Reaction Steps
A solution of 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (2.0 g, 4.60 mmol) in methanol (30 mL) was treated with a solution of 37% aqueous formaldehyde (7.5 mL, 100.72 mmol). The resulting mixture was heated to 100° C. for 18 h. At this time, the reaction mixture was cooled to 25° C. and was diluted with water. The resulting precipitate was collected by filtration, was washed with water and was dried in vacuo to afford 2-[3,5-dichloro-4-(1-hydroxymethyl-5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (1.97 g, 92%) as a light yellow solid. ES+-HRMS m/e calcd for C18H14N6O5Cl2 (M+H+) 465.0476, found 465.0475.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08076334B2 |
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| Source dataset | uspto-grants-2011_12 |
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| ORD ID | ord-9507adb4e895454fbb7062eaaba70069 |
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| Source note | uspto-grants-2011_12 |
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