Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Semicarbazide hydrochloride | HCID 11236 | — |
| 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 71699909 | HCID 71699909 | 60.2% |
Reaction Steps
To a solution of 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (35 mg, 0.115 mmol) in MeOH (3 mL), was added hydrazinecarboxamide hydrochloride (115 mg, 1.035 mmol). The solution was heated to 37° C. overnight. Triethyl amine (1 mL) was added and the solution was stirred at rt for 20 min. Solvents were removed in vacuo and the residue was diluted with DCM, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 25 mg of the title compound in 57% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.85 (s, 1H), 8.89 (m, 1H), 3.36 (d, 1H), 8.01 (m, 2H), 7.82 (d, 1H), 7.53 (dd, 1H), 6.17 (s, 2H), 2.32 (s, 3H). LCMS (method A): [MH]+=384, tR=4.09 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08497368B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-e760de9e5d124445a5619721fb714e70 |
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| Source note | uspto-grants-2013_07 |
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