Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | 3-[3-[[1-[2-(2-chloroethoxy)phenyl]cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide | HCID 66689804 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Azd-7624 | HCID 25143624 | — |
Reaction Steps
3-[3-[[1-[2-(2-chloroethoxy)phenyl]cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide (Example 259d, 10 g) in dioxane (25 mL) was treated with methylamine (15 mL of a 40 wt % aqueous solution). The resulting mixture was stirred at 100° C. for 16 h in a sealed tube. The reaction mixture was cooled, filtered and the solvents removed in vacuo to give crude product (˜10 g). The crude product (˜8.0 g) was purified by RPHPLC (Waters X-Bridge column, 95-5% gradient of aqueous 0.2% ammonia in acetonitrile as mobile phase). The product containing fractions were combined, evaporated and triturated with diethyl ether overnight. The white solid was collected by filtration and dried in vacuo to afford the title compound (4.14 g). NMR consistent with that described above in example 259.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889692B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-2777278dec4143169975cbe10e59365c |
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| Source note | uspto-grants-2014_11 |
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