Triethylamine → HCID 178495979, compound

Participants

Reaction Steps

A suspension of 4-(3-aminomethylphenyl)-2-[[(amino)(2-methoxyethylamino)methylene]amino]thiazole dihydrochloride (3.9 g), N-(t-butoxycarbonyl)glycine (1.85 g), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (2.6 g) and triethylamine (2.3 g) in N,N-dimethylformamide (50 ml) was stirred for 7 hours with cooling on an ice bath. The solvent was removed under reduced pressure. The residue was dissolved in a mixture of water (80 ml) and tetrahydrofuran (20 ml), and the mixture was alkalized with 30% aqueous potassium carbonate solution. The mixture was extracted with ethyl acetate (200 ml) and the extract was dried with magnesium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (20:1) to afford 2-[[(amino)(2-methoxyethylamino)methylene]amino]-4-(3-t-butoxycarbonylaminoacetylaminomethylphenyl)thiazole (1.65 g).

Provenance & Evidence