Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Serinol | HCID 68294 | — |
| Reactant | HCID 178513524 | HCID 178513524 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178513532 | HCID 178513532 | 27% |
Reaction Steps
To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indazole-7-carboxamide i (Intermediate 22) (19 mg, 0.0413 mmol) in DMF (1 mL) was added K2CO3 (25 mg, 0.165 mmol), 2-amino-1,3-propanediol (20 mg, 0.2065 mmol) and sodium iodide (1.0 mg). 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 (5.8 mg, 27%).
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-37a3b3f17d504b7dadf2e4253edd4168 |
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| Source note | uspto-grants-2013_08 |
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