Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 68292325 | HCID 68292325 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68292407 | HCID 68292407 | 83% |
Reaction Steps
(R)-methyl-3-((3-carbamoyl-6-(6-methoxypyridin-3-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-2,2-dimethylbutanoate (125 mg, 0.304 mmol) was dissolved in MeOH (25 mL) and water (1.0 mL). Potassium hydroxide (256 mg, 4.56 mmol) was added and the reaction mixture was heated at reflux overnight. After completion, the reaction mixture was cooled to room temperature and MeOH was removed under reduced pressure. The crude mass obtained was acidified to pH 5 at 0° C. using 1.5N HCl and stirred at room temperature for 15 minutes to give a solid that was collected by vacuum filtration and dried to afford the title compound (100 mg, 0.252 mmol, 83% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.13-1.15 (d, J=8.4 Hz, 6H), 1.25-1.26 (d, J=6.4 Hz, 3H), 3.86 (s, 3H), 4.68 (m, 1H), 6.84-6.86 (d, J=8.4 Hz, 1H), 7.25 (s, 1H), 8.06-8.064 (d, J=2 Hz, 1H), 8.15-8.18 (d, J=12 Hz, 2H), 8.59 (s, 1H), 10.86-10.89 (d, J=10 Hz, 1H). [α]24.8=1.6 (c=0.1, MeOH)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221826B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-04d2b1e5a1634dc9ba7902b077f76e24 |
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| Source note | uspto-grants-2015_12 |
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