Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 178488853 | HCID 178488853 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 178488852 | HCID 178488852 | 13.4% |
Reaction Steps
Ammonia (0.5M in 1,4-dioxane, 3.9 ml) was added to a stirred solution of 2-(8-methoxy-2-trifluoromethylquinolin-5-yl)-1H-benzimidazole-5-carboxylic acid (0.15 g) in 1,4-dioxane (30 ml) at room temperature under an inert atmosphere. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) was added followed by 4-dimethylaminopyridine (36 mg) and the reaction stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (2×40 ml) and water (50 ml). The combined organic phases were dried over magnesium sulphate and preadsorbed onto silica in vacuo. Purification by column chromatography eluting with 10% methanol in ethyl acetate afforded the title compound as a cream solid (20 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06069151 |
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| Source dataset | uspto-grants-2000_05 |
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| ORD ID | ord-e6ba5c5ff9134714b09d15173a1e481b |
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| Source note | uspto-grants-2000_05 |
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