1,4,7-Triazacyclononane → Ethyl 6-((4,7-bis((6-(ethoxycarbonyl)-4-(2,4,6-trimethoxyphenyl)-pyridin-2-yl)methyl)-1,4,7-triazonan-1-yl)methyl)-4-(2,4,6-trimethoxyphenyl)-pyridine-2-carboxylate

HRID 1097178Notes

Reaction equation

HRID 1097178 reaction equation
[NH:1]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19]([C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])[CH:18]=[C:17]([CH2:33]Br)[N:16]=1)=[O:14])[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13]([C:15]1[N:16]=[C:17]([CH2:33][N:1]2[CH2:9][CH2:8][N:7]([CH2:33][C:17]3[CH:18]=[C:19]([C:21]4[C:22]([O:31][CH3:32])=[CH:23][C:24]([O:29][CH3:30])=[CH:25][C:26]=4[O:27][CH3:28])[CH:20]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[N:16]=3)[CH2:6][CH2:5][N:4]([CH2:33][C:17]3[N:16]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH:20]=[C:19]([C:21]4[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=4[O:31][CH3:32])[CH:18]=3)[CH2:3][CH2:2]2)[CH:18]=[C:19]([C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1)=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 1883181,4,7-TriazacyclononaneHCID 590246614-(2,4,6-trimethoxyphenyl)-6-(bromomethyl)pyridine-2-carboxylic Acid Ethyl Ester

Product 1

HCID 11194088Ethyl 6-((4,7-bis((6-(ethoxycarbonyl)-4-(2,4,6-trimethoxyphenyl)-pyridin-2-yl)methyl)-1,4,7-triazonan-1-yl)methyl)-4-(2,4,6-trimethoxyphenyl)-pyridine-2-carboxylateYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4,7-triazacyclononane (31.5 mg) and compound 14 (0.3 g, 0.76 mmol) were dissolved in dry acetonitrile (20 mL) Potassium carbonate (0.17 g) was added and the mixture was refluxed overnight. The mixture was allowed to cool to room temperature, filtered and concentrated. Purification on silica gel (eluent CH2Cl2:EtOH:HOAc; 80:20:1, v/v/v) yielded the title compound (0.17 g, 62%). ESI-MS: [M+H]+ 1117.5 calc. for C60H73N6O15+ 1117.5

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed overnight
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel (eluent CH2Cl2:EtOH:HOAc; 80:20:1, v/v/v)

Sources & evidence

ORD record
ord-e097bc618e684315aa184359095ff97a
Source dataset
uspto-grants-2012_03
Patent number
US08143057B2

Reaction notes

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