Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Methoxybenzylamine | HCID 75452 | — |
| Reactant | HCID 89545051 | HCID 89545051 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 89544887 | HCID 89544887 | 58.8% |
Reaction Steps
Step 2 {(R)-[4-Chloro-3-(5-chloro-pyrazine-2-carbonyl)-2-fluoro-phenyl]-cyclopropyl-methyl}-carbamic acid tert-butyl ester (709 mg, 1.61 mmol), 4-methoxybenzylamine (0.232 ml, 1.77 mmol), triethylamine (0.448 ml, 3.22 mmol) and dimethylformamide (5 ml) was heated to 80 deg C for 3 hours. The reaction was allowed to cool, ethyl acetate was added, and the mixture was washed with 10% aqueous lithium chloride solution and brine. The organic liquors were dried (MgSO4) and concentrated. The residue was purified by column chromatography eluting with 10-50% ethyl acetate/petroleum ether furnishing ((R)-{4-Chloro-2-fluoro-3-[5-(4-methoxy-benzylamino)-pyrazine-2-carbonyl]-phenyl}-cyclopropyl-methyl)-carbamic acid tert-butyl ester (512 mg) as a yellow oil. [M+H]+ 541
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145354B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-afab2943eee94c2a8a5d5d0729d458d2 |
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| Source note | uspto-grants-2015_09 |
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