Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | HCID 178513524 | HCID 178513524 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 178513525 | HCID 178513525 | 28.5% |
Reaction Steps
To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indazole-7-carboxamide (Intermediate 22) (18 mg, 0.039 mmol) in acetonitrile (2 mL) was added K2CO3 (25 mg, 0.156 mmol), pyrrolidine (19 uL, 0.196 mmol) and sodium iodide (0.7 mg, 0.0039 mmol). The reaction mixture was heated to 60° C. overnight. 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 (5.5 mg, 28%).
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-544d666620c74680b7eb03fc5fdb538c |
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| Source note | uspto-grants-2013_08 |
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