Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-Chloro-6-isopropoxynicotinic acid | HCID 18070582 | — |
| Reactant | HCID 178471422 | HCID 178471422 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59316811 | HCID 59316811 | 70.3% |
Reaction Steps
5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (D31) (67.7 mg, 0.314 mmol) then triethylamine (88 μl, 0.628 mmol) followed by HOBT (57.7 mg, 0.377 mmol), EDC (72.3 mg, 0.377) and ethyl 4-{4-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}-2,2-dimethylbutanoate (D114) (100 mg, 0.314 mmol) were dissolved in DMF (4 ml) at room temperature then stirred at 50° C. for 5 days. The mixture was cooled to room temperature and diluted with EtOAc. The organic phase was washed with water, dried and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [15-40% EtOAc/cyclohexane] gave the title compound (110 mg, 67%) as a light yellow solid. MS (ES) C25H28ClN5O4 requires 497, found 498 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324254B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-3818491086834178956362dea9dc7253 |
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| Source note | uspto-grants-2012_12 |
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