N-(tert-Butoxycarbonyl)-1,5-diaminopentane → 4,5-Dihydro-4[5-(tert-butoxycarbonylamino)pentan-1-yl]-3H-1,4,8b-triazaacenaphthylen-5-one

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

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentane

HCID 8471Triethylamine

HCID 211901283-[(Trimethylammonio)methyl]-5-ethoxycarbonylimidazo[1,2-a]pyridine iodide

Product 1

HCID 211901734,5-Dihydro-4[5-(tert-butoxycarbonylamino)pentan-1-yl]-3H-1,4,8b-triazaacenaphthylen-5-oneYield 54.8%

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).