Methyl iodide → HCID 131724272, compound
Reaction equation
[OH:1][C@H:2]1[C@@H:9]2[N:5]([C:6](=[O:23])[N:7]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[C:8]2=[O:10])[CH2:4][CH2:3]1.I[CH3:25]>C(#N)C.[Ag-]=O>[CH3:25][O:1][C@H:2]1[C@@H:9]2[N:5]([C:6](=[O:23])[N:7]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[C:8]2=[O:10])[CH2:4][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
To a solution of compound 6C (100 mg, 0.326 mmol) in acetonitrile (2 mL), at RT, was added iodomethane (86 μL, 1.38 mmol), followed by silver(I) oxide (42 mg, 0.18 mmol). The mixture was refluxed at 85° C. for 16 hours. After cooling to RT, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give a crude product, which was purified by using a preparative HPLC (gradient, 20 to 90% of MeOH/H2O containing 0.1% of CF3CO2H over 10 minutes) to yield the title compound (racemate) (72 mg, 69% yield) as an off-white solid. mp. 185-186° C. HPLC: 99% at 2.45 min (retention time) (YMC S5 ODS column 4.6×50 mm; 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nM), MS (ES): m/z 322 [M+1]+.
Workup
- temperatureAfter cooling to RT
- filtrationthe reaction mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- customto give a crude product, which
- customwas purified
- customa preparative HPLC (gradient, 20 to 90% of MeOH/H2O containing 0.1% of CF3CO2H over 10 minutes)
Sources & evidence
- ORD record
- ord-af766273ea0d4615811caae3e7de8fc0
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06670386B2
Reaction notes
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