Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | HCID 1478615 | HCID 1478615 | — |
| Reactant | 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide | HCID 11368059 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 10207464 | HCID 10207464 | 26.2% |
Reaction Steps
Under Ar, the mixture of 3-(benzyloxy)thieno[2,3-b]pyridine-2-carboxylic acid (150 mg, 0.53 mmol) in 2 mL of N,N-dimethyl-formamide was heated to 80° C. Diphenylphosphoryl azide (146 mg, 0.53 mmol), 3-amino-6-chloro-2-hydroxybenzenesulfonamide (117 mg, 0.53 mmol) and triethyl amine (0.054 mL, 0.53 mmol) were added. The resulting mixture was heated for another 18 hours. when kept temperature at 70° C. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (70 mg, 26%). LC-MS (m/z) 505.2 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06608077B2 |
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| Source dataset | uspto-grants-2003_08 |
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| ORD ID | ord-5e7437694c1e49e6845a7260c55564cb |
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| Source note | uspto-grants-2003_08 |
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