Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Carbonochloridate | HCID 21226386 | — |
| Reactant | HCID 67443027 | HCID 67443027 | — |
| Product | HCID 67442475 | HCID 67442475 | 47.9% |
Reaction Steps
To a solution of the amine 343 (0.9 g, 1.69 mmol) in NMP (10 mL) at 0° C. was added pyridine (0.3 ml, 3.71 mmol) followed by the chloroformate (0.3 mL, 2.38 mmol). The mixture was stirred for 40 min at 0° C. then at room temperature for 120 min, quenched by addition of brine/NaHCO3 solution. A precipitate was formed which was collected by filtration and dried. The crude material was purified by flash column chromatography, eluent a 5 to 10% gradient of MeOH (containing 2% ammonia) in DCM, to afford the title compound 356 (0.528 g, 47.9% yield). MS (m/z): 653.6 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906852B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-f5557acacd3d41be9765541fd1507c52 |
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| Source note | uspto-grants-2014_12 |
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