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CAS No. : | 6928-85-4 | MDL No. : | MFCD00006154 |
Formula : | C5H13N3 | Boiling Point : | - |
Linear Structure Formula : | H2NN(CH2)4NCH3 | InChI Key : | RJWLLQWLBMJCFD-UHFFFAOYSA-N |
M.W : | 115.18 | Pubchem ID : | 81349 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-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 |
---|---|---|
With pyridine; In tetrahydrofuran; for 12.5h;Heating / reflux; | N- [5- (4-chloromethylbenzoylamino)-2-methylphenyl]-4- (3-pyridyl)-2-pyrimidine- amine (lg, 2. 33MMOL) was dissolved in tetrahydrofuran (20MQ), PYRIDINE (360, XE, 4. 66MMOL) was added thereto, and the mixture was stirred for 30 minutes. 1-AMINO-4-METHYLPIPERAZINE (418, UP, 3. 49MMOL) was added, and the mixture was refluxed for 12 hours and filtered. The filtrate was concentrated, subjected to column chromatography (eluent: chloroform : methanol=3 : 1 (v/v)), concentrated again, and then crystallized from dimethylether to give 4- (4-METHYLPIPERAZIN-1-YLAMINOMETHYL)-N- [4- METHYL-3- (4- (PYRIDIN-3-YL) pyrimidin-2-yl) aminophenyl] benzamide (880mg). Rf= 0.40 (Chloroform: Methanol =1 : 1) IH-NMR (CDCL3) = 2.31 (d, 6H), 7.48 (br, 8H), 3.54 (s, 2H), 7.06-7. 42 (m, 8H), 7.79- 7.83 (d, 2H), 8.07 (s, LH), 8. 46-8. 68 (m, 4H), 9.20 (m, LH) | |
With pyridine; In tetrahydrofuran; for 12.5h;Heating / reflux; | N- [5- (4-CHLORCNETHYLBENZAYLAMINO)-2-METHYLPHENYL]-4- (3-PYRIDYL)-2-PYRIMIDINE-A mine (lg, 2. 33MMOL) was dissolved in tetrahydrofuran (20 M), pyridine (360 mut, 4. 66MMOL) was added thereto, and the mixture was stirred for 30 minutes. L-AMINO-4-METHYLPIPERAZINE (418 mut, 3. 49MMOL) was added, and the mixture was refluxed for 12 hours and filtered. The filtrate was concentrated, subjected b column chromatography (eluent: chloroform : methanol=3: L (v/v) ), concentrated again, and then crystallized FRCM dimethylether to give 4-(4-methylpiperazin-1-ylaminomethyl)-N-[4- METHYL-3- (4- (PYRIDIN-3-YL) pyrimidin-2-yl) aminophenyl] benzamide (880mg). [175] [176] R = 0.40 (Chloroform : Methanol = 1 : 1) f [177] H-NMR (CDC1) = 2. 31 (d, 6H), 7.48 (br, 8H), 3.54 (s, 2H), 7.06-7. 42 (m, 8H), 7.79- 3 7.83 (d, 2H), 8.07 (s, 1H), 8.46-8. 68 (m, 4H), 9.20 (m, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In N,N-dimethyl-formamide; at 150 - 155℃;Inert atmosphere; | General procedure: A mixture of substituted indole 3-carboxaldehydes (1 mmol), the respective 1-amino-4-methyl piperazine (1.5 mmol) in 5 mL dry DMF was heated to reflux under N2 until no starting material could be detected by TLC. The resulting mixture was allowed to cool at room temperature and poured into water and extracted with EtOAc. The combined organic layers were washed with aqueous HCl (1N), saturated aqueous NaHCO3 and brine solution and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude product was purified by column chromatography using hexane/ethyl acetate (7:3) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydride; In N,N-dimethyl-formamide;Inert atmosphere; Reflux; | After dissolving <strong>[25365-71-3]2-phenyl-1H-indole-3-carboxaldehyde</strong> (1 mmol) in dimethylformamide (5 mL), 1-amino-4-methylpiperazine (1.5 mmol) was added and nitrogen gas was It was stirred and refluxed. After completion of the reaction, the mixture was cooled to room temperature, added with water, and extracted with ethyl acetate. The organic layer was washed with hydrochloric acid (1N), saturated sodium bicarbonate aqueous solution and sodium chloride aqueous solution, dried over anhydrous sodium sulfate, the solvent was filtered under reduced pressure, and the filtrate was subjected to column chromatography (hexane:ethyl acetate=3:1). Purification was carried out to obtain the target compound as a brown oil (85%). |
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