* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Step D: (S)-1-(3-aminophenyl)-1-aminoethane (S)-1-(3-nitrophenyl)-1-aminoethane (approx. 80% pure, 75.2 mg) was dissolved in THF (2 mL) and 10% Pd/C (13.8 mg) was added. The system was fitted with a balloon of hydrogen and purged 3*, the mixture left stirring 16 h at room temperature. Filtered the solution through Celite, washing thoroughly with methanol, and the solvent removed in vacuo. The residue was eluted on silica gel (3-6%(2M NH3 in MeOH)/CH2Cl2) to yield 23.7 mg of the title compound. 1H NMR (500 MHz, CDCl3): delta 7.13 (t, J=7.7 Hz, 1H); 6.74 (m, 1H); 6.71 (m, 1H); 6.58 (m, 1H); 4.03 (q, J=6.7 Hz, 1H); 3.68 (br s, 2H); 1.37 (d, J=6.7 Hz, 3H).
2
[ 317364-83-3 ]
[ 317830-29-8 ]
[ 317830-31-2 ]
Yield
Reaction Conditions
Operation in experiment
98%
With ammonia; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;
Step E: 2-[(S)-1-(3-aminophenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine <strong>[317830-29-8](S)-1-(3-aminophenyl)-1-aminoethane</strong> (23.7 mg) was dissolved in DMF (1 mL), diisopropylethylamine (90 muL) was added followed by 2-methylsulfonyl-4-[benzimidazol-1-yl]pyrimidine (43.2 mg). The resulting mixture was left heating at 100 C. for 65 h then cooled, concentrated in vacuo then the residue purified on silica gel twice (3% then 2% (2M NH3 in MeOH)/CH2Cl2) to yield 27.9 mg of the title compound (98%). 1H NMR (500 MHz, CDCl3, partial): delta 8.52 (br s, 1H); 8.39 (d, J=5.3 Hz, 1H); 7.83 (m, 1H); 7.36 (m, 2H); 7.18 (t, J=7.8 Hz, 1H); 6.84 (d, J=7.8 Hz, 1H); 6.77 (m, 2H); 6.61 (m, 1H); 1.61 (d, J=7.1 Hz, 3H).
8-chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine[ No CAS ]
[ 317830-29-8 ]
N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In dimethyl sulfoxide; at 60.0℃; for 5.0h;
90 mg of the 8-chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine [125-2] was dissolved in 3 mL of dimethylsulfoxide, then 46.6 mg of <strong>[317830-29-8]3-[(1S)-1-aminoethyl]aniline</strong> and 100 mg of potassium carbonate were added thereto, and stirred at 60C for 5 hours. The reaction mixture was cooled back to room temperature, and purified by preparative reversed phase liquid chromatography. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and 25 mg of N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine [125-3] was obtained as a brown oily product.
With potassium carbonate; In 1,4-dioxane; for 72.0h;Heating / reflux;
A mixture of 3-[(lS)-l-aminoethyl]aniline (7.5 g, 55 mmol), 2,6-dichloropyrazine (12.3 g, 82.5 mmol) and potassium carbonate (15.2 g, 110 mmol) in dioxane (140 mL) was <n="93"/>heated at reflux for 3 days. After this time the mixture was cooled to room temperature, filtered and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to giveN-[(15)-l-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (11.6 g, 85%) as a beige solid.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
