Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Cyclobutylamine | HCID 75645 | — |
| Reactant | HCID 178513524 | HCID 178513524 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178513529 | HCID 178513529 | 19% |
Reaction Steps
To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indazole-7-carboxamide (Intermediate 22) (20 mg, 0.0435 mmol) in DMF (1 mL) was added K2CO3 (27 mg, 0.174 mmol), cyclobutyl amine (18 uL, 0.217 mmol) and sodium iodide (0.8 mg, 0.00438 mmol). The reaction mixture was heated to 120° C. for 14 hrs. The solution was filtered and concentrated. The residue was purified by using a Gilson semi-preparative HPLC system with a YMC ODS-A (C-18) column 50 mm by 20 mm ID, eluting with 10% B to 80% B in 10 min, hold for 1 min where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (4.1 mg, 19%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08501780B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-458d533847ba467daa25bcf6bbc9bcbd |
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| Source note | uspto-grants-2013_08 |
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