Water → HCID 57846996, compound

HRID 550297Notes

Reaction equation

HRID 550297 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@H:6]1[C@H:15]2[CH2:16][CH2:17][N:18]([C:19]([C@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]3[NH:27][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])[C@H:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:7]1.[H-].[Na+].[CH3:38]I.O>CN(C=O)C>[CH3:38][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@H:6]1[C@H:15]2[CH2:16][CH2:17][N:18]([C:19]([C@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]3[NH:27][C:28](=[O:35])[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:20])[C@H:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11698468HCID 11698468, compound

Product 1

HCID 57846996HCID 57846996, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (119 mg, 0.252 mmol) synthesized in Example 81 in DMF (1 ml) was added sodium hydride (60% in oil, 12.1 mg, 0.30 mmol) under ice-cooling, and the mixture was stirred for 1 hr. Methyl iodide (0.0187 ml, 0.30 mmol) was added dropwise and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel and eluted with hexane-ethyl acetate (5:95, v/v) to give the title compound (76.5 mg, 63%) as an amorphous form.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (5:95

Sources & evidence

ORD record
ord-12723205de8f48908c9e6cb30d160913
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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