Trifluoroacetic acid → HCID 135800894, compound

HRID 2181338Notes

Reaction equation

HRID 2181338 reaction equation
COC1C=CC(C[O:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:55])[CH2:24][CH2:25][CH2:26][N:27]([C:29]4[CH:30]=[CH:31][C:32]([C:35]5[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43]CC6C=CC(OC)=CC=6)=[C:37]([O:53][CH3:54])[CH:36]=5)=[N:33][CH:34]=4)[CH3:28])=[CH:19][N:18]=3)=[CH:11][C:10]=2[O:56][CH3:57])=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:55])[CH2:24][CH2:25][CH2:26][N:27]([C:29]3[CH:30]=[CH:31][C:32]([C:35]4[CH:40]=[C:39]([O:41][CH3:42])[C:38]([OH:43])=[C:37]([O:53][CH3:54])[CH:36]=4)=[N:33][CH:34]=3)[CH3:28])=[CH:19][N:18]=2)=[CH:11][C:10]=1[O:56][CH3:57]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22485543HCID 22485543, compound

Product 1

HCID 135800894HCID 135800894, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N′-bis[2-[4-(4-methoxybenzyloxy)-3,5-dimethoxyphenyl]-5-pyridyl]-N,N′-dimethyl-1,3-propanediamine (72.0 mg, 0.089 mmol) in methylene chloride (1.0 mL) was added trifluoroacetic acid (1.0 mL). The reaction mixture was stirred at room temperature for 30 minutes, and concentrated under reduced pressure. A solution of the residue in chloroform was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield N,N′-bis[2-(4-hydroxy-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethyl-1,3-propanediamine as a pale yellow oil (43.0 mg, yield: 86%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washA solution of the residue in chloroform was washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d19ff166055a48af889f36de84df58d6
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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