Potassium Carbonate → 4-(6-Cyclobutanecarbonylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

A mixture of cyclobutanecarboxylic acid (0.5 ml), 1-hydroxybenzotriazole hydrate (0.8 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.0 g) in N,N-dimethylformamide (5 ml) was stirred for 1 hour at ambient temperature. The above mixture was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g) and triethylamine (1.8 ml) in N,N-dimethylformamide (15 ml) and the mixture was sitrred for 20 hours at ambient temperature. The reaction mixture was added a mixture of ethyl acetate tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was recrystallized from a mixture of N,N-dimethylformamide and ethyl acetate to give 4-(6-cyclobutanecarbonylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.86 g).

1. waitthe mixture was sitrred for 20 hours at ambient temperature
2. additionThe reaction mixture was added
3. washThe separated organic layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. customThe solvent was removed by concentration
6. customthe residue was recrystallized from a mixture of N,N-dimethylformamide and ethyl acetate

ORD record

ord-07832cf9745d4e0b9032086195224dc3

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05364871