Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Ethanol, 2-(aminooxy)-, hydrochloride | HCID 22507086 | — |
| Reactant | HCID 58190496 | HCID 58190496 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58190537 | HCID 58190537 | 74.3% |
Reaction Steps
A solution of 1-(7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl)ethanone (40 mg, 0.13 mmol), 2-(aminooxy)ethanol hydrochloride (30 mg, 0.26 mmol) and HCl (4 N in 1,4-dioxane, 0.1 mL) in methanol (5 mL) was stirred at room temperature for 48 h. The reaction mixture was neutralized with saturated aqueous NaHCO3 solution and diluted with water, extracted with dichloromethane, dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography in silica gel eluting with a ethyl acetate/methanol gradient to afford 35 mg (74%) of the title compound as yellow solid. 1H-NMR (400 MHz, d6-DMSO) δ ppm 8.94 (s, 1H), 8.84 (d, 1H), 8.28 (d, 1H), 7.97-7.91 (m, 3H), 7.77 (d, 1H), 7.49 (dd, 1H), 4.77 (t, 1H), 4.56 (s, 2H), 4.30-4.27 (m, 2H), 3.71-3.70 (m, 2H), 2.25 (s, 3H). LCMS (method B): [MH]+=363, tR=2.08 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08507676B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-75e8cd956de14bbbb38968e60935b74c |
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| Source note | uspto-grants-2013_08 |
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