Pyridine → HCID 12370533, compound

HRID 1357483Notes

Reaction equation

HRID 1357483 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[C:28](Cl)(=[O:30])[CH3:29].N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]4)=[CH:20][CH:21]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12370530HCID 12370530, compound

Product 1

HCID 12370533HCID 12370533, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

35 mg (0.10 mmol) of 9-[4-(piperazin-1-yl)phenyl]aminoacridine (Example 16) was dissolved in 2 ml of chloroform, 7.1 μl (0.10 mmol) of acetyl chloride and catalytical amounts of pyridine and triethylamine were added. After 2 h of stirring at room temperature, the solvents were removed under vacuum, and the residue was purified by silica gel chromatography (eluent chloroform: methanol 6:1). The fractions with the title compound were combined, evaporated, taken up to water and extracted with chloroform. After drying over sodium sulfate, the organic layer was evaporated to obtain the title compound (6%, overall yield 1%).

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was purified by silica gel chromatography (eluent chloroform: methanol 6:1)
  3. customevaporated
  4. extractionextracted with chloroform
  5. dry with materialAfter drying over sodium sulfate
  6. customthe organic layer was evaporated

Sources & evidence

ORD record
ord-6a53555256054b0082fd542caff01ba8
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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