Structure of 503615-03-0
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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. : | 503615-03-0 |
| Formula : | C15H17N3O4 |
| M.W : | 303.31 |
| SMILES Code : | [O-][N+](=O)C1=CC=C(C=C1)N1CCC=C(N2CCOCC2)C1=O |
| MDL No. : | MFCD19440872 |
| InChI Key : | LBFAEOWNWSDWRZ-UHFFFAOYSA-N |
| Pubchem ID : | 21936809 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | 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 |
|---|---|---|
| 98% | With hydrazine hydrate; In methanol; water; at 40 - 70℃; for 3h;Large scale; | Add 25L of water and 25L of methanol to the 500L reactor, add 2.5kg of compound (I) and 250g of Raney cobalt under stirring, raise the temperature to 40-50 C, slowly add 2.0kg of hydrazine hydrate (content 80%), keep warm 60-70 C, reaction for 3h, the reaction was completed, filtered with diatomaceous earth, concentrated solvent was removed, and MTBE was added to the filter cake.2.20 kg of a white solid were obtained with a yield of 98% and a purity of 99.8%. |
| 95.55% | With hydrazine hydrate; In ethanol; water; at 60 - 65℃; for 0.5h; | Hydrazine hydrate 80% (60 gm, 1.19 mol) was added drop wise at around 60-65 C. to the solution containing product of example-III (50 gm, 0.16 mol), Raney nickel (1 gm, 2%) in EtOH (750 ml) and water (150 ml). After completion of addition, stirred for 30 min at same temperature and brought to room temperature. The reaction mass was filtered through celite bed, concentrated under vacuum, added EtOAc (100 ml) and filter under suction. Dried the wet cake in air oven to afford the desired product as a cream colored solid. Yield: 43 gm; 95.55% |
| 94% | With sodium sulfide; SPGS-550-M; water; at 50 - 55℃; | 3-(Morpholin-4-yl)- 1 -(4-nitrophenyl)-5 ,6-dihydropyridin-2( 1H)-one (10 g; Formula II) was added to a reaction vessel containing an aqueous solution of SPGS-550M(20 mL, 2 wt. % in water) at ambient temperature. Sodium sulphide (20 g) was added. The reaction mixture was heated to 50C to 55C and stirred for 3 hours to 4 hours. The reaction mixture was cooled to ambient temperature. The reaction mixture was filtered, washed with dc-ionized water (30 mL), and then dried in an air oven at 45C to 50C to obtain the title compound.Yield: 94% |
| 93.2% | With sodium disulfide; water; In ethanol; at 50 - 55℃; for 3h;Large scale; | 2000L reactor by adding purified water 570kg,Stirring under the addition of sodium hexahydrate 569.7kg,Heating to 50-55 C, stirring about 30 minutes to dissolve, add sulfur 76kg, stirring and stirring for 1 hour to dissolve, prepared to obtain sodium disulfide.Followed by adding ethanol 570kg,90 kg of the compound of formula II-1,50-55 C Insulation reaction 3h,The reaction was complete and extracted with 900 kg of dichloromethane.The organic layer was washed with 500 kg of saturated brine and dried over 50 kg of anhydrous sodium sulfate for 2 hours. The dichloromethane was distilled off under reduced pressure to give 75.6 kg of the 1-1 compound, the yield was 93.2%, and the HPLC purity was 100%.As shown in Figure 1, almost no impurities in the product produced, the raw material reaction is complete. |
| 91% | With sodiumsulfide nonahydrate; In ethanol; at 60℃; for 1h; | Compound 6 (10g, 0.033mol), NaS.9H2O (32g, 0.13mol), Anhydrous ethanol 200mol added to the reaction bottle, adding reaction bottle, 60 C reaction 1h, The ethanol was evaporated and the product was worked up as a pale yellow solid (8.3g, 0.03mol) in a yield of 91% |
| 91% | With sodiumsulfide nonahydrate; In methanol; water; at 40 - 45℃; for 2.75h; | A solution of Sodium sulfate nonahydrate (197 g, 2.5 eq) in water (350 ml_) was dosed over 45 minutes at T=40/45C into a mixture of compound of formula (XI) (100 g,1.0 eq.) and methanol (1000 mL). The mixture was stirred at T=40/45C for additional 2 hours to reach reaction completion. The mixture was then distilled at reduced pressure and Tmax=45C until 930 ml_ of solvent were removed. The resulting slurry was cooled down to T=20/25C, kept stirring for 1 hour at this temperature and then filtered washing the wet cake with water (2 x 100 mL). Upon drying at reduced pressure and T=65C for 10 hours, 82 g of the compound of formula (X) were obtained. (91 % yield, HPLC A%: compound of formula (X) 96.16%, Said compound of formula (X) thus obtained contained the following dimer impurities: - 0,66% (HPLC A/A%) dimer impurity of formula (VI), - 1 ,50% (HPLC A/A%) dimer impurity of formula (VII). |
| 74.1% | With sodium sulfide; water; In ethanol; at 50℃;Inert atmosphere; | The 1d (18.0g, 59.3mmol) was dissolved in ethanol (180ml) was added sodium sulfide nonahydrate (28.4g, 118.6mmol), was added water (60ml) to give a reaction mixture, and the mixture was reacted at 50 C .The reaction was refluxed overnight. Tracking progress of the reaction by TLC, the reaction was completed, the ethanol under reduced pressure, extracted three times with ethyl acetate, the combined organic phases concentrated to remove, dried over anhydrous magnesium sulfate, filtered, and the solvent removed by distillation under reduced pressure to give 1e (12.0g, yellow solid) yield: 74.1% |

[ 503615-03-0 ]
[ 27143-07-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With tetrabutylammomium bromide; sodium carbonate; In dichloromethane; at 20℃; for 10h; | 50 mL of dichloromethane was added to the reaction flask, The intermediate I was added successively with stirring (5.00 g, 0.0165 mol), Intermediate II (5.88 g, 0198 mol), Sodium carbonate (5.25 g, 0.095 mol) And tetrabutylammonium bromide (1. 06 g, 0.0033 mol) were added and stirred at room temperature for 10 h TLC determines the reaction is complete. To the reaction flask slowly dropping dilute hydrochloric acid to the system pH 2 ~ 3, The reaction was complete after TLC was allowed to react at room temperature for 2 h. The reaction was stopped and 50 mL of water was added. The organic layer was separated and washed with water (2 X 50 mL) The organic layer was dried over anhydrous sodium sulfate. Filtration, the filtrate under pressure to remove the solvent by rotary distillation of yellow solid, And recrystallized from ethyl acetate and dried to give 6. 47 g of a pale yellow solid compound C. |
[ 503615-03-0 ]
[ 27143-07-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94.6% | Compound V (20 g, 0.078 mol) was added to a 500 mL eggplant flask, Ethyl acetate (240 ml),KI (1.2 g, 6.5 mmol),Compound IV (19.6 g, 0.065 mol) and triethylamine (18.2 mL, 0.14 mol) were further added,Warm to reflux for 4.5 h.The reaction solution was cooled to 5 ° C,4N HCl (80 ml, 0.32 mol) in water was added dropwise,After dropping at room temperature for 4h. To the reaction solution was added 300 mL of water,Dichloromethane 3 × 200mL extraction,300mL saturated brine wash,Dried over anhydrous sodium sulfate,Dry dichloromethane to give crude,Then 60mL ethyl acetate slurry,27.2g of product,m.p. 188-191 ° C,Yield 94.6percent. |
Tags: 503615-03-0 synthesis path| 503615-03-0 SDS| 503615-03-0 COA| 503615-03-0 purity| 503615-03-0 application| 503615-03-0 NMR| 503615-03-0 COA| 503615-03-0 structure

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| P101 | If medical advice is needed,have product container or label at hand. |
| P102 | Keep out of reach of children. |
| P103 | Read label before use |
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| P202 | Do not handle until all safety precautions have been read and understood. |
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| P211 | Do not spray on an open flame or other ignition source. |
| P220 | Keep/Store away from clothing/combustible materials. |
| P221 | Take any precaution to avoid mixing with combustibles |
| P222 | Do not allow contact with air. |
| P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
| P230 | Keep wetted |
| P231 | Handle under inert gas. |
| P232 | Protect from moisture. |
| P233 | Keep container tightly closed. |
| P234 | Keep only in original container. |
| P235 | Keep cool |
| P240 | Ground/bond container and receiving equipment. |
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| P243 | Take precautionary measures against static discharge. |
| P244 | Keep reduction valves free from grease and oil. |
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| P263 | Avoid contact during pregnancy/while nursing. |
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| P270 | Do not eat, drink or smoke when using this product. |
| P271 | Use only outdoors or in a well-ventilated area. |
| P272 | Contaminated work clothing should not be allowed out of the workplace. |
| P273 | Avoid release to the environment. |
| P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
| P281 | Use personal protective equipment as required. |
| P282 | Wear cold insulating gloves/face shield/eye protection. |
| P283 | Wear fire/flame resistant/retardant clothing. |
| P284 | Wear respiratory protection. |
| P285 | In case of inadequate ventilation wear respiratory protection. |
| P231 + P232 | Handle under inert gas. Protect from moisture. |
| P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
| Code | Phrase |
| P301 | IF SWALLOWED: |
| P304 | IF INHALED: |
| P305 | IF IN EYES: |
| P306 | IF ON CLOTHING: |
| P307 | IF exposed: |
| P308 | IF exposed or concerned: |
| P309 | IF exposed or if you feel unwell: |
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| P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
| P321 | |
| P322 | |
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| P332 | IF SKIN irritation occurs: |
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| P335 | Brush off loose particles from skin. |
| P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
| P337 | If eye irritation persists: |
| P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
| P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P342 | If experiencing respiratory symptoms: |
| P350 | Gently wash with plenty of soap and water. |
| P351 | Rinse cautiously with water for several minutes. |
| P352 | Wash with plenty of soap and water. |
| P353 | Rinse skin with water/shower. |
| P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
| P361 | Remove/Take off immediately all contaminated clothing. |
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| P371 | In case of major fire and large quantities: |
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| P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
| P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
| P378 | |
| P380 | Evacuate area. |
| P381 | Eliminate all ignition sources if safe to do so. |
| P390 | Absorb spillage to prevent material damage. |
| P391 | Collect spillage. Hazardous to the aquatic environment |
| P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
| P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
| P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
| P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
| P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
| P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
| P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
| P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
| P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
| P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
| P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
| P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
| P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
| P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
| P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
| P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
| P370 + P376 | In case of fire: Stop leak if safe to Do so. |
| P370 + P378 | In case of fire: |
| P370 + P380 | In case of fire: Evacuate area. |
| P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
| P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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| P411 | |
| P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
| P413 | |
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| P422 | |
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| P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
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| H200 | Unstable explosive |
| H201 | Explosive; mass explosion hazard |
| H202 | Explosive; severe projection hazard |
| H203 | Explosive; fire, blast or projection hazard |
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| H222 | Extremely flammable aerosol |
| H223 | Flammable aerosol |
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| H226 | Flammable liquid and vapour |
| H227 | Combustible liquid |
| H228 | Flammable solid |
| H229 | Pressurized container: may burst if heated |
| H230 | May react explosively even in the absence of air |
| H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
| H240 | Heating may cause an explosion |
| H241 | Heating may cause a fire or explosion |
| H242 | Heating may cause a fire |
| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
| H261 | In contact with water releases flammable gas |
| H270 | May cause or intensify fire; oxidizer |
| H271 | May cause fire or explosion; strong oxidizer |
| H272 | May intensify fire; oxidizer |
| H280 | Contains gas under pressure; may explode if heated |
| H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
| H300 | Fatal if swallowed |
| H301 | Toxic if swallowed |
| H302 | Harmful if swallowed |
| H303 | May be harmful if swallowed |
| H304 | May be fatal if swallowed and enters airways |
| H305 | May be harmful if swallowed and enters airways |
| H310 | Fatal in contact with skin |
| H311 | Toxic in contact with skin |
| H312 | Harmful in contact with skin |
| H313 | May be harmful in contact with skin |
| H314 | Causes severe skin burns and eye damage |
| H315 | Causes skin irritation |
| H316 | Causes mild skin irritation |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
| H330 | Fatal if inhaled |
| H331 | Toxic if inhaled |
| H332 | Harmful if inhaled |
| H333 | May be harmful if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
| H340 | May cause genetic defects |
| H341 | Suspected of causing genetic defects |
| H350 | May cause cancer |
| H351 | Suspected of causing cancer |
| H360 | May damage fertility or the unborn child |
| H361 | Suspected of damaging fertility or the unborn child |
| H361d | Suspected of damaging the unborn child |
| H362 | May cause harm to breast-fed children |
| H370 | Causes damage to organs |
| H371 | May cause damage to organs |
| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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