Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66989510 | HCID 66989510 | — |
| Reactant | 4-Amino-6-chloro-5-cyanopicolinic acid | HCID 71464210 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58503938 | HCID 58503938 | — |
Reaction Steps
A solution of 1,1′-carbodiimidazole (0.15 g) and 4-amino-6-chloro-5-cyanopicolinic acid (0.14 g, prepared according to the reported preparation in Zhao, Hongyu, et al.; J. Med. Chem. 2006, 49(15), 4455-4458) in N,N-dimethylformamide (3.5 mL) was stirred one hour at room temperature. The compound prepared in Example 392 (0.30 g) and triethylamine (0.60 mL) were added and the reaction was stirred for one hour more. A saturated sodium bicarbonate solution was added and the mixture was vigorously stirred overnight. The mixture was diluted with water and then filtered. The solids were evaporated from acetone and then a 1:1 dichloromethane:toluene solution. The solids were triturated with dichloromethane to furnish the title compound (0.22 g) having the following physical data.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809538B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-fe0e4f048e2a4e4e9429cdb28c10e214 |
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| Source note | uspto-grants-2014_08 |
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