HCID 23155415, compound → HCID 23155556, compound

HRID 2080749Notes

Reaction equation

HRID 2080749 reaction equation
[CH2:1]([N:4]([CH2:31][CH2:32][CH3:33])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH3:30])[C:11]2[CH:17]=[C:16]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:2][CH3:3]>CN.CO>[NH2:19][CH2:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:31][CH2:32][CH3:33])[N:10]([CH3:30])[C:11]=2[CH:17]=1

Participants

3

Reactant 1

HCID 23155415HCID 23155415, compound

Product 1

HCID 23155556HCID 23155556, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 57454252Monomethylamine methanolSolvent

Procedure

The compound (232 mg) obtained in Example 13-5 was dissolved in a 40% methylamine/methanol solution (3.0 ml) and the whole was stirred at room temperature for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (17.0 mg) as a pale-yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-b0fa49d4caab44e5ab490afed853c019
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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