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CAS No. : | 926037-48-1 | MDL No. : | MFCD27956910 |
Formula : | C27H21F3N8O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DUPWHXBITIZIKZ-UHFFFAOYSA-N |
M.W : | 530.50 | Pubchem ID : | 16063245 |
Synonyms : |
IY-5511
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
85% | Example 2[69] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)benzamide[70][71] Method A[72] A pale yellow solid final compound (18.7g, yield 85%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 4-methyl -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)-benzoic acid ethyl ester in a similar manner as described in Method A of Example 1, except that 4-methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino) -benzoic acid ethyl ester (15.3g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester.[73] 1H-NMR(DMSOd , delta= 2.21(s,3H), 2.38(s,3H), 7.35(s,lH), 7.39(s,lH), 7.54(s,lH),7.63(d,lH), 7.75(d,lH), 8.14(d,2H), 8.38(d,2H), 8.54(d,2H), 8.68(s,lH), 9.06(s,lH), 9.45(s, IH), 10.56(s,lH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Method B[76] A pale yellow solid final compound (18.3g, yield 83%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 4-methyl -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)-benzoic acid methyl ester in a similar manner as described in Method A of Example 1, except that 4-methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino) -benzoic acid methyl ester (14.7g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Method D[82] A pale yellow solid final compound (16. Ig, yield 73%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 4- methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)benzoic acid phenyl ester in a similar manner as described in Method A of Example 1, except that 4-methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino) -benzoic acid phenyl ester (17.5g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.4% | With sodium hydroxide In ethanol for 32h; Reflux; | 1.3; 2.3; 3.3 (3) Synthesis of Ladotinib: Dissolve stannous chloride in absolute ethanol, add 5g SBA-15 mesoporous molecular sieve, stir for 3h, dry in 70 oven for 8h, and roast in 400 muffle furnace for 3h to obtain mesoporous molecular sieve catalyst with 10% tin content . 77g of 3-dimethylamino-1-(3-pyrazinyl)-2-propene-1-one, 847g of ethanol, 51g of sodium hydroxide, 8g of mesoporous molecular sieve catalyst and 208g of Intermediate II, put them into the reaction flask and raise the temperature Reflux for 32h. After the reaction is over, filter while hot, and the filtrate is cooled and frozen to crystallize. The crude product of radotinib was obtained by suction filtration, washed with water, and then refined and decolorized with 5 times the volume of ethanol to obtain 224 g of finished product of radotinib, with a yield of 97.4% and a purity of 99.89%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 4 h / Reflux 1.2: 8 h / Reflux 2.1: nitric acid / ethanol; water / 20 h / 20 °C 3.1: sodium hydroxide / ethanol / 32 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 4 h / Reflux 1.2: 8 h / Reflux 2.1: nitric acid / ethanol; water / 20 h / 20 °C 3.1: sodium hydroxide / ethanol / 32 h / Reflux |