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CAS No. : | 467235-09-2 | MDL No. : | |
Formula : | C9H11N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 161.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
67% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 0 - 20℃; for 5h; Inert atmosphere; | 68; 69 6-Chioro-N-(4-cyano-2-(ethylamino)phenyl)pyridazine-4-carboxamide 11104] To a stirred solution of 4-amino-3-(ethylamino) benzonitrile Int-4 (200 mg, 1.24 mmol) in EtOAc (10 mE) under an inert atmosphere was added 6-chioropyridazine-4- carboxylic acid (210 mg, 1.32 mmol), triethylamine (0.34 mE, 2.48 mmol) and propylphosphonic anhydride (50% in EtOAc, 1.97 mE, 3.10 mmol) at 00 C. The reaction mixture was stirred at room temperature for 5 h. Afier consumption of starting material (by TEC), the reaction mixture was quenched with saturated sodium bicarbonate solution (30 mE) and extracted with EtOAc (2x30 mE). The combined organic extracts were washed with water (40 mE), brine (40 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 20% EtOAc/hexane) to afford 6-chloro-N-(4-cyano-2-(ethylamino)phenyl) pyridazine-4-carboxamide (250 mg, 0.83 mmol, 67%) as a yellow solid.11105] ‘H NMR (500 MHz, DMSO-d5): ö 10.23 (brs, 1H),9.65 (d, J=i.2 Hz, 1H), 8.39 (s, 1H), 7.40 (d, J=8.i Hz, 1H),7.06-6.99 (m, 2H), 5.77 (br s, 1H), 3.20-3.15 (m, 2H), 1.17(t, J=7.0 Hz, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred solution of <strong>[157335-92-7]4-methylpyrimidine-5-carboxylic acid</strong> (86 mg, 0.62 mmol) in DMF (2 mL) under an inert atmosphere was added HATU (354 mg, 0.93 mmol) at room temperature and stirred for 30 min. 4-Amino-3-(ethylamino)benzonitrile Int-10 (100 mg, 0.62 mmol) and ethyldiisopropylamine (0.22 mL, 1.24 mmol) were added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 16 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford N-(4-cyano-2-(ethylamino)phenyl)-4-methylpyrimidine-5-carboxamide (150 mg, crude) as a brown syrup which was used directly without further purification. LC-MS: m/z 282.1 [M+H]+ at 2.12 RT (65.87% purity). |