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CAS No. : | 317830-29-8 | MDL No. : | MFCD06761850 |
Formula : | C8H12N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MBWYRMCXWROJMP-LURJTMIESA-N |
M.W : | 136.19 | Pubchem ID : | 40637894 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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). |
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). |
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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen;palladium 10% on activated carbon; In methanol; for 19.0h; | A mixture of (IS)-I -(3-nitrophenyl)ethanamine (13.1 g, 79.4 mmol) and 10% palladium on carbon (0.75 g) in methanol (250 mL) was stirred vigorously under an atmoshphere of hydrogen for 19 hours. After this time the mixture was filtered through a pad of Celite and the pad was washed with methanol (800 mL). The combined filtrates were concentrated under reduced pressure to give 3-[(lS)-l-aminoethyl]aniline as a brown solid (10.8 g, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.91 g of the 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [80-3] was dissolved in 60 mL of chloroform, 1.77 g of m-chloroperbenzoic acid was added under an ice-cold condition, and stirred at 0C for 30 minutes. After adding 100 mL of a saturated aqueous solution of sodium hydrogen carbonate and 100 mL of water, the reaction solution was extracted with a mixture solvent of chloroform and methanol (chloroform : methanol = 9:1). After drying the organic layer over anhydrous sodium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 60 mL of tetrahydrofuran, and added to 20 mL of a tetrahydrofuran solution prepared by 1.11 g of <strong>[317830-29-8]3-[(1S)-1-aminoethyl]aniline</strong> (synthesized according to a method disclosed in Pamphlet of International Publication WO 00/056,331, pages 67-70) and 1.65 mL of triethylamine. The mixture was stirred at room temperature for 3 hours, 100 mL of a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the insolubles were filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by preparative reversed phase liquid chromatography. The obtained eluent was basified with a saturated aqueous solution of sodium bicarbonate, and then extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After the insolubles were filtered, and the filtrate was concentrated under reduced pressure, the residue was dissolved under heating in ethanol, and allowed to stand still at room temperature. The precipitate was filtered and dried under reduced pressure to obtain 1.2 g of the target compound [80] as a white solid. A spectral data of the compound [80] is presented below. 1H-NMR (CDCl3) delta: 9.89 - 9.80 (m, 1H×1/5), 8.90 - 9.02 (m, 1H+1H×4/5), 8.62 (s, 1H×1/5), 8.57 (s, 1H×4/5), 7.55 - 7.10 (m, 3H), 6.88 - 6.02 (m, 4H), 6.06 - 5.97 (m, 1H×4/5), 5.86 - 5.75 (m, 1H×1/5), 5.25 - 5.18 (m, 1H×1/5), 5.02 - 4.88 (m, 1H×4/5), 3.76 (brs, 2H), 1.61 (d, J = 6.8Hz, 3H) mass: 406 (M+1)+. |