Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 58777346 | HCID 58777346 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58777355 | HCID 58777355 | 91% |
Reaction Steps
To a solution of intermediate 194, (R)-(1-(2-((3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamido)methyl)-5-fluorophenyl)-5-oxopyrrolidin-2-yl)methyl methanesulfonate (0.150 g, 0.239 mmol) in DMF (10 mL) was added sodium azide (0.019 g, 0.287 mmol). The resulting mixture was stirred at 50° C. for 6 h. Water (50 mL) was then added and the organic material was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.125 g, 91% yield). LCMS (M+H)+ m/z 576.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07176196B2 |
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| Source dataset | uspto-grants-2007_02 |
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| ORD ID | ord-745e340cc72e4c2cbff84455007fd8f9 |
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| Source note | uspto-grants-2007_02 |
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