Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | O-Methylhydroxylamine hydrochloride | HCID 521874 | — |
| Reactant | 1-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone | HCID 59341802 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 71811139 | HCID 71811139 | 75.7% |
Reaction Steps
To a solution of 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (6.3 mg, 0.021 mmol) in methanol (3 mL) was added O-methylhydroxylamine hydrochloride (16.7 mg, 0.20 mmol), followed by addition of triethyl amine to adjust the pH to 5-6. The reaction mixture was stirred at 30° C. for 3 h. The solvent was removed under reduced pressure and the residue was dissolved in DCM. The resulting solution was washed with NaHCO3 solution, water and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by prep-HPLC to afford 5.3 mg (69%) of the title compound. 1H-NMR (400 MHz, CD3Cl) δ ppm 9.67 (s, 1H), 8.94 (m, 1H), 8.16 (t, 2H), 7.93 (d, 1H), 7.86 (dd, 1H), 7.53 (dd, 1H), 6.11 (s, 2H), 4.14 (s, 3H), 2.38 (s, 3H). LCMS (method A): [MH]+=334, tR=5.02 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-8328e633529b468dade7952f66c7faab |
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| Source note | uspto-grants-2013_08 |
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