4-Aminopyridine → HCID 22054176, compound

HRID 1830352Notes

Reaction equation

HRID 1830352 reaction equation
[Cl-].ClC1N(C)CC[NH+]1C.[NH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[C:27](=[O:50])[C:28]([CH3:49])=[C:29]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[C:38]([O:45]C(=O)C)[CH:37]=2)[C:30](=[O:34])[C:31]=1[O:32][CH3:33]>C(Cl)(Cl)Cl.C(Cl)Cl>[N:14]1[CH:15]=[CH:16][C:11]([NH:10][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][C:36]([CH2:35][C:29]3[C:30](=[O:34])[C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[C:27](=[O:50])[C:28]=3[CH3:49])=[CH:37][C:38]=2[OH:45])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054194HCID 22054194, compound

Product 1

HCID 22054176HCID 22054176, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1,3-dimethylimidazolinium chloride (43 mg, 0.257 mmol), 4-aminopyridine (24 mg, 0.257 mmol) and triethylamine (26 mg, 0.257 mmol) were added to a methylene chloride solution (5 ml) of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (64 mg, 0.171 mmol) in a nitrogen atmosphere and the resulting solution was stirred all the night through. The reaction solution was diluted with chloroform, then washed with water and dried, and the solvent was removed by distillation. Subsequently, an aqueous saturated sodium hydrogencarbonate solution (10 ml) was added to a methanol solution (4 ml) of the obtained residue and the resulting solution was stirred for 1 hour. The reaction solution was extracted with ethyl acetate, then washed with water and dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1) to obtain the titled compound (5 mg, 0.012 mmol, 7.2%).

Workup

  1. washwashed with water
  2. customdried
  3. customthe solvent was removed by distillation
  4. additionSubsequently, an aqueous saturated sodium hydrogencarbonate solution (10 ml) was added to a methanol solution (4 ml) of the obtained residue
  5. stirringthe resulting solution was stirred for 1 hour
  6. extractionThe reaction solution was extracted with ethyl acetate
  7. washwashed with water
  8. customdried
  9. customthe solvent was removed by distillation
  10. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-62d1e89f54264143ab674a8b41855c13
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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