Methyl iodide → HCID 178487818, compound

HRID 2273245Notes

Reaction equation

HRID 2273245 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[N:10]=[C:11]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]1[NH:16][C:15](=[O:23])[CH:14]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:30]4[C:38](=[O:39])[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]4=[O:40])[CH2:26][CH2:25]3)[O:13][C:12]2=1.IC.ClCCl>CN(C)C=O.CO>[CH3:7][O:8][C:9]1[N:10]=[C:11]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]1[N:16]([CH3:1])[C:15](=[O:23])[CH:14]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:30]4[C:38](=[O:39])[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]4=[O:40])[CH2:26][CH2:25]3)[O:13][C:12]2=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 178487817HCID 178487817, compound

Product 1

HCID 178487818HCID 178487818, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

Sodium carbonate (405 mg, 3.82 mmol, 3.5 eq) is added at −5° C. to a stirred solution of 2-[trans-4-(6-methoxy-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione (500 mg, 1.09 mmol, 1.0 eq) in N,N-dimethylformamide (30 mL), followed by iodomethane (408 μL, 6.55 mmol, 6.0 eq). After 14 hours stirring at −5° C., solvent is removed and the residue is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 2-[trans-4-(6-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione as a light red semisolid (420 mg, 81% yield).

Workup

  1. customsolvent is removed
  2. extractionthe residue is extracted with ethyl acetate (3×100 mL) and water (100 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude that
  8. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-1e63320880374e7aaac6638e3a3321e9
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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