Methyl iodide → HCID 58981040, compound

HRID 1181808Notes

Reaction equation

HRID 1181808 reaction equation
[H-].[Na+].[C:3]([NH:7][S:8]([C:11]1[N:12]=[C:13]([C:17]2[N:18]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[N:19]=[C:20]3[C:25]=2[C:24](=[O:26])[N:23]([CH3:27])[C:22](=[O:28])[N:21]3[CH2:29][CH:30]([CH3:32])[CH3:31])[N:14]([CH3:16])[CH:15]=1)(=[O:10])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:44]I>CN(C=O)C>[C:3]([N:7]([CH3:44])[S:8]([C:11]1[N:12]=[C:13]([C:17]2[N:18]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[N:19]=[C:20]3[C:25]=2[C:24](=[O:26])[N:23]([CH3:27])[C:22](=[O:28])[N:21]3[CH2:29][CH:30]([CH3:32])[CH3:31])[N:14]([CH3:16])[CH:15]=1)(=[O:9])=[O:10])([CH3:5])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58980907HCID 58980907, compound

Product 1

HCID 58981040HCID 58981040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (10 mg, 0.25 mmol) was added to a solution of the compound of Example 164 (84 mg, 0.14 mmol) and CH3I (100 μL) in 2 mL DMF. After warming to room temperature and stirring for 16 h, solvent was removed and the residue was partitioned between water and EtOAc. The EtOAc was separated and washed with brine. Drying and removal of solvent gave an oil that was purified by preparative reverse phase HPLC (45%-75% gradient of CH3CN-water with 0.1% TFA).

Workup

  1. customsolvent was removed
  2. customthe residue was partitioned between water and EtOAc
  3. customThe EtOAc was separated
  4. washwashed with brine
  5. customDrying
  6. customremoval of solvent
  7. customgave an oil that
  8. customwas purified by preparative reverse phase HPLC (45%-75% gradient of CH3CN-water with 0.1% TFA)

Sources & evidence

ORD record
ord-ff61d2860d744deead3d5fb95dd6c5c5
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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