Triethylamine → HCID 46927538, compound

HRID 1910723Notes

Reaction equation

HRID 1910723 reaction equation
[NH2:1][CH:2]1[C:15]2[C:6](=[CH:7][CH:8]=[C:9]3[C:14]=2[CH:13]=[CH:12][CH:11]=[N:10]3)[N:5]([C:16](=[O:18])[CH3:17])[CH:4]([CH3:19])[CH2:3]1.C(N([CH2:25][CH3:26])CC)C.[Cl-:27].[NH4+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Cl:27][C:26]1[CH:25]=[CH:4][C:3]([NH:1][CH:2]2[C:15]3[C:6](=[CH:7][CH:8]=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[N:10]4)[N:5]([C:16](=[O:18])[CH3:17])[CH:4]([CH3:19])[CH2:3]2)=[CH:2][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66700112HCID 66700112, compound

Product 1

HCID 46927538HCID 46927538, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

[Step 5] 36 mg (0.14 mmol) of the 1-(1-amino-3-methyl-2,3-dihydro-4,7-phenanthrolin-4(1H)-yl)ethanone, 51 mg (0.28 mmol) of copper (II) acetate, 43 mg (0.42 mmol) of triethylamine and 2 ml of a dichloromethane suspension containing 27 mg of molecular sieve (4A) were vigorously stirred for 18 hours. Following completion of the reaction, aqueous ammonium chloride solution was added followed by extraction with chloroform. The extract was washed with water and the organic layer was dehydrated with anhydrous sodium sulfate. The residue obtained by concentrating under reduced pressure was purified by silica gel column chromatography (ethyl acetate) and NH silica gel column chromatography (n-hexane:ethyl acetate=2:1) followed by crystallizing with diethyl ether and n-hexane to obtain 7 mg of the target compound in the form of a pale yellow crystalline powder (13%).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform
  3. washThe extract was washed with water
  4. customThe residue obtained
  5. concentrationby concentrating under reduced pressure
  6. customwas purified by silica gel column chromatography (ethyl acetate) and NH silica gel column chromatography (n-hexane:ethyl acetate=2:1)
  7. customby crystallizing with diethyl ether and n-hexane

Sources & evidence

ORD record
ord-93528862df48439499f515c13fdf2c2b
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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