Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Phenoxyethanamine | HCID 15651 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide | HCID 86646022 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58451297 | HCID 58451297 | 179.6% |
Reaction Steps
To a solution of bis(trichloromethyl) carbonate (30 mg, 0.102 mmol) in tetrahydrofuran (2 mL) was added dropwise a suspension of N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.290 mmol) produced in Example 16(vi) and triethylamine (100 μL, 0.725 mmol) in tetrahydrofuran (2 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. 2-Phenoxyethanamine (45 μL, 0.348 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hr. Ethyl acetate (6 ml) and water (4 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. The precipitated solid was collected by filtration to give the title compound (93 mg, 63%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697874B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-345fd4c447d445c5a5b1baa7d938d0e9 |
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| Source note | uspto-grants-2014_04 |
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