Water → HCID 178517036, compound

HRID 1878026Notes

Reaction equation

[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][CH2:9][C:10]2([C:25]([F:28])([F:27])[F:26])[C:15]3[CH:16]=[C:17]([C:20]([NH:22]C)=O)[CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:24])[O:11]2)=[O:7])=[CH:4][CH:3]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][C:10]2([C:25]([F:26])([F:27])[F:28])[C:15]3[CH:16]=[C:17]([C:20]4[NH:33][N:32]=[N:31][N:22]=4)[CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:24])[O:11]2)=[O:7])=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 110 °C

Procedure

N-{[6-cyano-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (30 mg, 0.076 mmol) synthesized in Example 159, sodium azide (24.8 mg, 0.38 mmol) and ammonium chloride (20.4 mg, 0.38 mmol) were dissolved in DMF (0.5 mL), and the solution was stirred for 12 hours under heating at 110° C. Water was added to the solution and the solution was extracted twice with ethyl acetate-ethanol, and the resulting organic layer was dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by reverse-phase HPLC, whereby the objective compound (3.4 mg, 10%) was obtained as a white solid.

Workup

extractionthe solution was extracted twice with ethyl acetate-ethanol
dry with materialthe resulting organic layer was dried over magnesium sulfate
customAfter the drying agent was removed by filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by reverse-phase HPLC, whereby the objective compound (3.4 mg, 10%)
customwas obtained as a white solid

Sources & evidence

ORD record: ord-301b2b35027245d7b8a79d1bd93e5622
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314094B2

Reaction notes

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