Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 57919906 | HCID 57919906 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57919796 | HCID 57919796 | — |
Reaction Steps
To a solution of 2-(3-(4-fluorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-4-methylthiazole-5-carboxylic acid in N,N-dimethylformamide is added N,N-diisopropylethylamine, followed by the addition of 1-hydroxybenzotriazole monohydrate and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The resulting mixture is stirred for 10 minutes and followed by the addition of benzylamine at ambient temperature. After stirred at ambient temperature for an additional 17 h, the mixture is concentrated in vacuo. The residue is poured into a saturated aqueous solution of sodium bicarbonate and then extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated and purified by column chromatography to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08049016B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-69a81ae2d9e54294b36f50fb4a1bdae0 |
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| Source note | uspto-grants-2011_11 |
|---|