Dimethylformamide → HCID 136005949, compound

HRID 915950Notes

Reaction equation

HRID 915950 reaction equation
CN(C)C=O.[CH:6]1([N:12]2[C:20]3[C:19](=[O:21])[NH:18][C:17]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)=[CH:24][C:23]=4[O:35][CH3:36])=[N:16][C:15]=3[C:14]([CH3:37])=[N:13]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:38](N(CC)CC)[CH3:39].C(I)C>C(OCC)(=O)C>[CH:6]1([N:12]2[C:20]3[C:19](=[O:21])[NH:18][C:17]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:34][CH2:33][CH2:32][N:31]([CH2:38][CH3:39])[CH2:30][CH2:29]5)=[CH:24][C:23]=4[O:35][CH3:36])=[N:16][C:15]=3[C:14]([CH3:37])=[N:13]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 8471TriethylamineHCID 136043092HCID 136043092, compound

Product 1

HCID 136005949HCID 136005949, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 4 ml N,N-dimethylformamide solution of 102 mg (0.23 mmol) of the compound obtained in Example 125, 49 μl (0.35 mmol) of triethylamine and 23 μl (0.29 mmol) of ethyl iodide were added at room temperature, and the mixture was stirred for 3 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and a saturated aqueous solution of sodium chloride in this order. The washed system was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1˜10/1) to obtain 65 mg (60%) of the captioned compound.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe washed system was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1˜10/1)

Sources & evidence

ORD record
ord-5a6636a01b8342688b6312f704a6be89
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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