Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 1H-Indazole-6-carbaldehyde | HCID 18538368 | — |
| Reactant | HCID 68733542 | HCID 68733542 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178517177 | HCID 178517177 | 24.2% |
Reaction Steps
A scintillation vial was charged with 2-oxo-N-phenylindoline-5-carboxamide (22 mg, 0.087 mmol), 1H-indazole-6-carbaldehyde (14 mg, 0.096 mmol), piperidine (1 uL, 0.008 mmol) and MeOH (2 mL). The reaction was then heated to 60° C. for 2 hrs. A yellow precipitate formed which was further precipitated by cooling to room temperature and adding more MeOH (2 mL). The yellow solid was then filtered and washed with MeOH (10 mL) to give 8.0 mg, 24% of the title compound. 1H NMR (400 MHz, d6-DMSO) δ 13.42 (s, 1H), 11.02 (s, 1H), 10.16 (s, 1H), 9.01 (s, 1H), 8.39 (s, 1H), 8.14 (s, 2H), 8.03 (d, J=7.3 Hz, 1H), 7.89-7.82 (m, 2H), 7.79 (d, J=6.5 Hz, 2H), 7.36 (t, J=6.6 Hz, 2H), 7.11-7.09 (m, 1H), 6.96 (d, J=6.9 Hz, 1H); MS ESI 381.1 [M+H]+, calcd for [C23H16N4O2+H]+ 381.14.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765748B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-97de415c82a04d22839b3a687da05961 |
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| Source note | uspto-grants-2014_07 |
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