Structure of 39562-22-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 39562-22-6 |
Formula : | C14H15NO6 |
M.W : | 293.27 |
SMILES Code : | CC(/C(C(OCCOC)=O)=C\C1=CC=CC([N+]([O-])=O)=C1)=O |
MDL No. : | MFCD00521048 |
InChI Key : | UVZJPCAZMGLNTB-UKTHLTGXSA-N |
Pubchem ID : | 2063485 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
91% | With dimethyl amine; In ethanol; isopropyl alcohol; | a) 200 kg of 2-methoxyethyl acetoacetate and 185.1 kg of 3-nitrobenzaldehyde are suspended in 800 l of isopropanol. Then 5.65 kg of p-anisic acid and 5.05 kg of 33percent dimethylamine in ethanol are added, heating for about 30' at about 35° C. to obtain a solution. The reaction mixture is left to cool at 20/25° C. and then it is cooled for about 12 hours with running water and for a further 24 hours at about 0° C. with brine, then is centrifuged, washing with isopropanol. After drying, 327 kg of 2-methoxyethyl 2-(3-nitrobenzylidene) acetoacetate are obtained, in an about 91percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(b) 270 ml of isopropanol and 64.4 g (0.45 mole) of isopropyl 3-aminocrotonate are added to the 2-methoxyethyl 2-(3'-nitrobenzylidene)acetoacetate which has been prepared according to (a) and is moist with isopropanol. The mixture is heated to reflux (83° C.) and kept at this temperature for 24 hours. After cooling to 0° C., the resulting crystals are isolated, washed with 86 ml of isopropanol and sucked dry. 173.2 g of 3-isopropyl, 5-(2-methoxy)-ethyl 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-3,5-pyridine dicarboxylate of melting point 122°-127° C. (92percent of theory) are obtained. Thin-layer chromatography on Merck silica gel ready-coated plates (mobile phase: chloroform:acetone:petroleum ether=3:2:5) shows no visible by-products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | (a) 1,4-Dihydro-2,6-dimethyl-3-(2-methoxyethoxy)-carbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine Prepared by a method analogous to that of Example 1(a) from 7.0 g (24 mmol) of <strong>[39562-22-6]2-(3-nitrobenzylidene)-acetoacetic acid-(2-methoxyethyl)ester</strong> and 6.55 g (24 mmol) of 3-aminocrotonic acid-(2-phthalimidoethyl)ester in ethanol. 11.08 g (84percent) of pale yellow crystals, melting point 182°-184° C. C28 H27 N3 O9 (549.54). Rf (CH2 Cl2 /CH3 OH 95:5): 0.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | 1. In a 250 ml bottle, added material a: 2-(3-nitrophenylmethylene)acetoacetic acid methyl ester (54g, 0.184mol) and material b:3-amino-2-butenoic acid cinnamyl ester (40g, 0.184mol) and anhydrous ethanol (80g), heating reflux 1 hour; 2. To step 1 added concentrated hydrochloric acid to the reaction system (> 35percent) 3.31 ml, continue to reflux for 1 hour, the rear cooling crystallization, filtering to obtain cilnidipine crude; thick quantity : 80.7g; yield 88.98percent ; M.P.: 106.1-106.7 °C; maximum shan Za : 0.2percent, a total of 10 small impurity peak, content: 99.25percent.Receiving product: 80.77gYield 89.07percent,M.P.: 106.0-106.8 °CThe maximum shan Za : 0.29percentA total of 9 small impurity peakContent: 99.18percent 3. In accordance with the weight ratio of ethanol: crude = 3:1 use anhydrous ethanol is added in the amount in step 2 the horizontal thick Sydney obtained in recrystallization, to get finished product Cini the horizontal.Yield 91.5percent,M.P.: 107.4-108.2 °CThe maximum shan Za : 0.1460percentThe minimum shan Za : 0.0502percentA total of 2 a small impurity peakContent: 99.8percent |