Reaction equation
[I-].C[N+:3]([CH2:6][C:7]1[N:11]2[C:12]([C:16]([O:18]CC)=O)=[CH:13][CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)([CH3:5])C.[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32]CN)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>>[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:5][N:3]1[C:16](=[O:18])[C:12]2[N:11]3[C:7](=[CH:8][N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]Participants
4
Procedure
A solution of 7.78 g (20 mmol) of 3-[(trimethylammonio)methyl]-5-ethoxycarbonylimidazo [1,2-a]pyridine iodide, 6.07 g (30 mmol) of 5-tert-butoxycarbonylamino-1-pentylamine and 5.58 ml (40 mmol) of triethylamine was heated for 64 hours under reflux. The solvent was distilled off. To the residue was added methylene chloride, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 3.93 g of the desired compound (54.9%, a pale yellow solid).
Workup
- temperatureunder reflux
- distillationThe solvent was distilled off
- additionTo the residue was added methylene chloride
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)
Sources & evidence
- ORD record
- ord-fe3959d2b56d42c4b63412223c5abdc6
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958942
Linked notes
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