Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 178513508 | HCID 178513508 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178483611 | HCID 178483611 | 49% |
Reaction Steps
To a solution of 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indazole-7-carboxamide (Intermediate 7) (200 mg, 0.432 mmol) in DMF (5 mL) was added K2CO3 (250 mg), sodium iodide (10 mg), and 2M dimethyl amine in DMF (1 mL) The reaction mixture was heated to 60° C. overnight. The solution was filtered. The filtrate 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 40% B to 80% B in 3.2 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 (100 mg, 49%)
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-401995e94f214ce8886d185f5220a586 |
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| Source note | uspto-grants-2013_08 |
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