Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenyl pyridin-3-ylcarbamate | HCID 6935890 | — |
| Reactant | HCID 66974054 | HCID 66974054 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 49839067 | HCID 49839067 | 39% |
Reaction Steps
To a solution consisting of 3-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-pyrrolidine (111 mg, 0.399 mmol), triethylamine (0.1 mL, 0.72 mmol) and acetonitrile (2 mL) was added pyridin-3-yl-carbamic acid phenyl ester (90.1 mg, 0.421 mmol). The mixture was heated at 35° C. for 18 h, cooled to rt and then concentrated. The crude residue was purified (FCC) to give the title compound (56 mg, 39%). MS (ESI): mass calcd. For C18H17F2N3O3, 361.12. m/z found, 362.2 [M+H]+. 1H NMR (CD3OD): 8.63-8.59 (m, 1H), 8.16-8.13 (m, 1H), 7.97-7.92 (m, 1H), 7.35-7.30 (m, 1H), 7.16-7.09 (m, 2H), 7.06-7.02 (m, 1H), 3.66-3.53 (m, 2H), 3.48-3.38 (m, 1H), 3.19-3.11 (m, 1H), 2.85-2.72 (m, 2H), 2.62-2.50 (m, 1H), 2.11-2.02 (m, 1H), 1.78-1.66 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901111B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-9a1c1f5776ab4074bfc167c3e544fc78 |
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| Source note | uspto-grants-2014_12 |
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