Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid | HCID 86679365 | — |
| Reactant | HCID 86680214 | HCID 86680214 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71539639 | HCID 71539639 | 80.3% |
Reaction Steps
To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (82 mg, 0.297 mmol) and (6-tert-butyl-2-m-tolylpyridin-3-yl)methanamine (76 mg, 0.297 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (85 mg, 0.445 mmol), 1-hydroxybenzotriazole (60 mg, 0.445 mmol) and triethylamine (0.1 mL, 0.742 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-((6-tert-Butyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 23) (122 mg) was obtained as 80% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08937092B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-c4650a74e8964d5e8c3b72a5cb7f64ce |
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| Source note | uspto-grants-2015_01 |
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