Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 22239044 | HCID 22239044 | — |
| Reactant | Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate | HCID 58046667 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | HCID 58046615 | HCID 58046615 | 84% |
Reaction Steps
To a solution of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.14 g, 0.33 mmol), potassium carbonate (0.068 g, 0.5 mmol) and sodium iodide (0.015 g, 0.01 mmol) in 2-butanone (3 mL), was added 1-(3-chloropropyl)-1H-indazole (0.065 g, 0.33 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered, concentrated and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.16 g, 84%); 1H NMR (DMSO-d6): δ 1.51 (s, 9H), 1.59 (d, 2H, J=12.8 Hz), 2.03 (t, 2H, J=6.4 Hz), 2.24 (t, 2H, J=7.2 Hz), 2.57-2.67 (m, 4H), 3.56 (t, 2H, J=6.4 Hz), 4.47-4.63 (m, 6H), 6.78 (t, 1H, J=7.2 Hz), 6.85-6.87 (m, 2H), 7.11 (t, 1H, J=8 Hz), 7.24 (t, 2H, J=8 Hz), 7.34 (t, 1H, J=7.6 Hz), 7.48-7.51 (m, 2H), 7.70-7.83 (m, 4H), 8.07 (s, 1H); MS for C35H41N5O3 m/z 580.14 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691836B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-3b86f6954c984c5b9424842a631d8d84 |
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| Source note | uspto-grants-2014_04 |
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