Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4-(1-Ethyl-propylamino)-3-(2-pyrazol-1-yl-acetylamino)-benzoic acid methyl ester | HCID 86714423 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86714424 | HCID 86714424 | 90% |
Reaction Steps
To 2.28 g 4-(1-Ethyl-propylamino)-3-(2-pyrazol-1-yl-acetylamino)-benzoic acid methyl ester were added 50 ml of 4M hydrochloric acid in dioxane. Divided into five portions the reaction mixture was heated to 110° C. for 15 min in a microwave reactor. After cooling to the reaction mixture 6 ml of 10 M aqueous sodium hydroxide solution were added slowly. After 30 min at rt the reaction mixture was concentrated to a third of its volume and adjusted to pH 4 by the addition of 2M aqueous hydrochloric acid. It was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. 1.86 g (90%) of 1-(1-Ethyl-propyl)-2-pyrazol-1-ylmethyl-1H-benzoimidazole-5-carboxylic acid were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156796B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-30ef379bab3a49799918bb2d9372776d |
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| Source note | uspto-grants-2015_10 |
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