Structure of 212322-56-0
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CAS No. : | 212322-56-0 |
Formula : | C18H22N4O3 |
M.W : | 342.39 |
SMILES Code : | O=C(OCC)CCN(C1=NC=CC=C1)C(C2=CC=C(NC)C(N)=C2)=O |
MDL No. : | MFCD09833624 |
InChI Key : | PCPATNZTKBOKOY-UHFFFAOYSA-N |
Pubchem ID : | 11982993 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-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 |
---|---|---|
95% | Step 1 : Crude product 10.0 g of N-(4-cyanophenyl)glycine and 10.35 g of N,N'-carbonyldiimidazole (CDI) are mixed at room temperature in 150 mL of isopropyl acetate. Then, 19.43 g of ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate are added and the mixture reacts for 4 hours at room temperature. After this time, 20 mL of acetic acid are added and the mixture is refluxed for 2 hours. It is allowed to cool at room temperature and 33 mL of water are added. The organic phase is separated and further 33 mL of water are added. The pH of the mixture is adjusted to 10-11 with a dissolution of 25% of sodium hydroxide, forming a suspension. The suspension is filtered and the solid obtained is dried at 45 C in a vacuum oven. Yield: 24.6 g of crude base of the compound (III); (90% yield). Product purity: 94% measured by HPLC. Melting point: 1 16 C measured by differential scanning calorimetry technique (DSC); X-rays (angle 2-theta values ()): 7.6, 10.2, 10.9, 14.6, 15.2, 20.5, and 25.5 measured on a x-ray diffractometer with Cu K alpha radiation (1.5418 A). - Step 2: Purification of the compound (III) in free base form The crude product is recrystallized from 100 mL of ethanol, and a white solid with a high purity of 99% (HPLC) is obtained. Yield: 23,4 g of the purified base of the compound (III); (95% recrystallization yield). Product purity: 99% measured by HPLC; Melting point: 148C measured by differential scanning calorimetry technique (DSC); X-rays (angle 2-theta values ()): 5.9; 12.0; 13.7; 16.8; 18.9; 19.5; 21 .3; 24.4, and 27.6 measured on a x-ray diffractometer with Cu K alpha radiation (1.5418 A). | |
93.97% | Take SM02 (20.00g, 58.41mmol) in a 100ml single-mouth bottle, toluene (60ml) was added, magnetically stirred at ambient temperature, and set aside.At room temperature, SM01 (12.35g, 70.09mmol), CDI (11 · 84g, 73 · 01mmol) and toluene (120.0ml) were added to the reaction flask. Stirred and heated to 50 C. After 2-4 h, the reaction was monitored by TLC and the reaction was completed. The heating was stopped, the temperature of the reaction solution was lowered to 25 C, the toluene solution of SM02 was quickly added, and the mixture was stirred at 20-25 C for 5-16 h. The reaction was monitored by TLC. After completion of the reaction, acetic acid (8.0 ml) was added, and the reaction mixture was heated to 100 C, and kept for 1-2 h. The reaction was monitored by TLC. After completion of the reaction, the reaction solution was cooled to room temperature and then concentrated, the residue was dissolved in a solvent, and the solvent used were dichloromethane, chloroform, 1, 2-dichloroethane or the like. The resulting solution was adjusted to pH 7, using a saturated aqueous solution of sodium bicarbonate, after layering, the aqueous phase was extracted once with dichloromethane, and the organic phase was combined; Washed once with water, after stratification, the aqueous phase was extracted once more with dichloromethane, organic phases were combined, the solvent was concentrated under reduced pressure to give DB02 crude material. | |
91.1% | In a 500 ml reaction flask,23.2 g (0.132 mol) of N- (4-cyanophenyl) -aminoacetic acid were added,100 ml of dimethylformamide,19.6 g (0.145 mol) of 1-hydroxybenzotriazole was added at 3 C,A solution of 29.9 g (0.145 mmol) of dicyclohexylcarbodiimide in 50 ml of dimethylformamide was added dropwise.Stirring reaction 1h,Slowly rose to room temperature,A solution of 50.0 g (0.145 mol) of compound 3 in dimethylformamide (100 ml) was added dropwise,The reaction was stirred for 6 h.The reaction solution was filtered,The filtrate was added dropwise to 750 ml of water at 1 C,Insulation 1 hour,filter.300 ml of toluene and 20.0 g of glacial acetic acid were heated to 90 C,Incubation reaction 6 hours,After cooling to room temperature, 120 g of water was added,40 ml of ammonia was added dropwise to adjust pH to 9,Stirring to precipitate a solid,Cooling 2 ,Holding 2 hours,filter,Drying was a gray solid .0g,The yield was 91.1%Directly used in the next step reaction. |
86% | This embodiment's darbey adds the group ester method for the preparation of intermediates with the following steps:(1) under the protection of nitrogen, the 28.3g the N-(4-cyano-phenyl)-glycine (0.16mol) and 25.9g condensing agent CDI (0.16mol) dissolved in the 100 ml of methylene chloride and 100 ml of a mixed solvent of the ether in a, stirring and heating to 40 ±2 C reflux, thermal insulation reaction 1-2h.(2) added to the above-mentioned reaction system 50.0g of 3-amino-4-methyl amino-benzoic acid-N-(2-pyridyl)-N - (2-ethoxy carbonyl-ethyl)-amide (0.14mol), in 40 ±2 C continue to return to the temperature of the condensation reaction, to 3-amino-4-methyl amino-benzoic acid-N-(2-pyridyl)-N - (2-ethoxy carbonyl-ethyl)-amide reaction is complete, to stop the reaction.Generating compound IV does not need separation directly used for the next step.(3) in the above-mentioned reaction system is added to 160 ml of acetic acid, first decompression concentrating evaporating methylene chloride and ethyl ether, then heating to 50-60 C to cyclization reaction, until the compound IV the reaction is complete, to stop the reaction.(4) after the reaction, water is poured in the reaction system, cooling to 20-30C, crystallization, filtration, the filter cake after re-crystallization with ethanol, again filtered, the filter cake is drying to obtain 60.6g compound I, to yield 86.0%, | |
85% | (1) at room temperature,75 g of compound of formula 6,1000 mL THF,100mL triethylamine mixed,Cooled to 0 ,70mL pivaloyl chloride was added below 10 and the reaction was incubated for 0.5h; After the reaction was completed, 155g of compound of formula 4 was added,45 reaction 2h;The organic layer was evaporated to dryness and added to 1500mL n-butyl acetate, at 90 for 4h,700 mL of butyl acetate was distilled off under reduced pressure,The crystals were stirred at 5 C,Filtered and dried to give a dry product of formula 3 175g,The yield is 85%; | |
83% | 4-Nitriloanilino-acetic acid (2.32 g, 13.2 mmol) was dissolved in 80 ml of DMF,1-Hydroxybenzotriazole (H0BT) (1.96 g, 14.5 mmol) was added,Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI) (2.77 g, 14.5 mmol) was added at 0 C under stirring for 45 min,Slowly rise to room temperature,Ethyl 3- (1-methylamino-2-amino-phenyl-4-yl) -carboxylic acid- (N-2-pyridyl) amidopropionic acid ethyl ester (5.50111111.01) was added at room temperature the reaction overnight, concentrated, diluted with ethyl acetate and large, washed three times with brine, dried over Na2S04 after dried, concentrated and the crude product in 60ml of acetic acid was refluxed for 1.5h, was concentrated, basified added 1.5N aqueous ammonia, extracted three times with ethyl acetate. (60 mL X 3). The organic phase was washed once with brine, dried over Na 2 SO 4 and concentrated. The crude product was purified by silica gel column chromatography.The amorphous solid, 3- (1-methyl-2- (4-nitrile-phenylaminomethyl) -5-yl-carboxylic acid- (N-2-pyridyl) amido) propionic acid ethyl ester (6.4 g, yield 83%). Mass spectrum (ESI-MS): 482 ? 1 (M + H) +, 505.4 (M + Na) +; C27H26N6O3 (482) | |
61% | a) 1-Methyl-2-[N-(4-cyanophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide Prepared analogously to Example 25c from N-(4-cyanophenyl)-glycine and 3-amino-4-methylamino-benzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide. Yield: 61% of theory, Rf value: 0.62 (silica gel; dichloromethane/methanol=19:1) | |
Example 1 - Large-scale industrial synthesis of the compound of formula 4-Br88 kg carbonyl-di-(l,2,4-triazole) are taken and combined with 920 1 tetrahydrofuran. The contents of the apparatus are heated to 35C with stirring. Then 90 kg of compound 3 are added batchwise at 35C within 1 to 2 hours.160 kg of compound 2 are placed in a second reaction vessel, then 350 1 tetrahydrofuran are added and the mixture is heated to 500C with stirring.The solution of 3 is metered into the solution of 2 within 2 to 3 hours at 47C - 53C and the solution obtained is diluted with 115 1 tetrahydrofuran. Then the mixture is stirred for another 4 hours at 47C - 53C ( preferably 500C ). Then 670 1- 695 1 tetrahydrofuran are distilled off in vacuo at 50C-60C. 235 1 of n-butyl acetate are then allowed to flow into the residue. After this, 600 1 -630 1 of a butyl acetate/THF mixture are distilled off in vacuo at 50C-85C. During the distillation 700 1 butyl acetate are metered in. 65 kg acetic acid are allowed to flow into the residue, the contents are heated to 85C-90C and stirred for at least another 2.5 h at this temperature. Then the mixture is cooled to 65C-75C. A solution of 165 1 water and 20 kg common salt is added to the contents and the mixture is rinsed with 300 1 water. Then the temperature is adjusted to 60C-70C and the mixture is stirred for a minimum of 15 min. at this temperature. For phase separation the stirrer is stopped and the mixture is left to settle for at least 15 min. The aqueous phase is drained off into another reaction vessel which contains 120 1 of n-butyl acetate. The mixture is heated to 60C-70C with stirring and stirred for at least 10 min. After phase separation the aqueous phase is drained off into the chemical waste drain. The butyl acetate phases and 20 1 of butyl acetate for rinsing are combined. 590 1 - 620 1 of n-butyl acetate are distilled off from this content in vacuo at a max. internal temperature of 800C. <n="12"/>880 1 isopropanol are allowed to flow into the distillation residue and the content is adjusted to 32C-38C. Then approx. 90 kg of 48% hydrobromic acid are metered in at 32C-38C until the pH value is 0.6 to 1.3. The mixture is stirred for a minimum of 20 min. at 32C-38C and then cooled to 7C-13C and stirred at this temperature for at least one hour. The resulting suspension is centrifuged, washed with a total of 840 1 isopropanol and dried in vacuo at max. 55C. Yield: 211 kg-250 kg. Mp.: 200-2150C (with decomposition).The compound 4-HBr may be isolated using any standard commercially available centrifuge. | ||
Example 1 : Ethyl N-[(2-[(p-cyanophenyl)amino1methyl)-1 -methyl-1 H- benzimidazole-5-carbonyl1-N-(2-pyridyl)-3-aminopropionate hydrochloride (IV-HCI)Under Ar atmosphere, A/-(p-cyanophenyl)-glycine (V) (7.22 g, 41 .0 mmol) and 1 ,1 '-carbonyldiimidazole (6.64 g, 41 .0 mmol) were suspended in anhydrous THF (315 mL). It was refluxed for 45 minutes and a solution of compound (VI) (12.74 g, 37.2 mmol) in anhydrous THF (56 mL) was added slowly. After 6 h under reflux, the reaction mixture was cooled down, and the solvent was distilled under low pressure. The oil obtained was dissolved in glacial acetic acid (155 mL) and refluxed for 1 h. The solvent was removed under low pressure, the residue was dissolved in CH2CI2 (130 mL) and washed with H2O (2 x 130 mL). The organic phase was dried over anhydrous MgSO4 and the solvent was distilled under low pressure. The residue obtained was dried under vacuum, obtaining 20.19 g of crude (IV) (75% a/a purity according to HPLC/MS).The brown oil was dissolved in isopropanol (101 mL) at 35 C and HCI(c) (37%, 3.40 mL, 41 .1 mmol) was added slowly. After a short time an abundant white solid appeared. It was stirred at 35 C for 30 min and next at 0 C for 30 min. The solid was filtered out, washed with IPA (15 mL) and dried under vacuum, obtaining the product (IV-HCI) (14.25 g, 74% yield, 97% a/a purity according to HPLC/MS). This solid was recrystallized from EtOH (160 mL), washed with EtOH (2 x 10 mL) and dried under vacuum, obtaining 12.13 g (23.4 mmol, 63% global yield, 99% a/a purity according to HPLC/MS) of the product (IV-HCI).1H RMN (400 MHz, CD3OD) : delta (ppm) = 8.33 (ddd, J = 4.8, 2.0, 0.8, 1 H), 7.77 (d, J = 8.8, 1 H), 7.66 (dd, J = 1 .6, 0.8, 1 H), 7.60 (ddd, J = 8.0, 8.0, 2.0, 1 H), 7.55-7.50 (m, 3H), 7.17 (ddd, J = 7.6, 4.8, 0.8, 1 H), 7.09 (d, J = 8.0, 1 H), 6.83 (d, J = 8.8, 2H), 5.02 (s, 2H), 4.34 (t, J = 7.2, 2H), 4.05 (q, J = 7.2, 2H), 4.02 (s, 3H), 2.76 (t, J = 7.2, 2H), 1 .19 (t, J = 7.2, 3H).Melting point (Tme,t): 213-215 CPXRD: FIG. 2, 2theta angle values () = 3.7, 10.0, 10.9, 17.7, 18.3, 20.9, 22.0, 22.5, 23.7, 25.9, 26.4. | ||
Example-20: Preparation of l-methyI-2-[N-(4-cyanophenyl) aminomethyl] benzimidazol-5-ylcarboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide compound of formula-14 A mixture of 2-(4-cyanophenylamino)acetic acid (139 g) and tetrahydrofuran (750 ml) was heated to 50-55C. A solution of N,N'-carbonyldiimidazole (177.6 g) in tetrahydrofuran (1000 ml) was added to the above reaction mixture at the same temperature over a period of 1 hour and stirred for 2 hours at 50-55C. A solution of ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido) propanoate compound of formula- 12 (250 g) in tetrahydrofuran (1500 ml) was added over a period of 2 hours at 50-55C and heated to 60-65C. The reaction mixture was stirred for 50 hours at 60- 65C. After completion of the reaction, distilled off the solvent from the reaction mixture. Acetic acid was added to the reaction mixture and heated to 95-100C. The reaction mixture was stirred for 5 hours at 95-100C. Distilled off the solvent completely under the reduced pressure and the reaction mixture was cooled to 25-30C. Water was added to the reaction mixture and the product was extracted with dichloromethane. Dichloromethane layer was washed with water followed by sodium chloride. Distilled off the solvent completely from the dichloromethane layer to obtain title compound.Yield: 300 g | ||
Example-4: Process for preparation of the crystalline ethyl 3-(2-((4-cvanophenylamino)methylVl- methvl-N-(pvridin-2-vO-lH-benzotdUmidazole-5-carboxamido) propanoate of Formula (2B) 77 g 2-(4-cyanophenylamino) acetic acid of Formula (E), 71.04 g CDI in 1000 mL Toluene were stirred at 25C to 35C. The reaction mixture was heated to 55C to 60C and maintained for 2 hours. 100 g ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2- yl)benzamido)propanoate of Formula (2A) was added to the reaction mixture and stirred for 3 hours at 60C to 65C. The reaction mixture was further heated at 100C for 3 hours. Toluene was distilled under vacuum. The residue was treated with 500 mL methylene dichloride and organic layer was washed with water. The organic layer was filtered and washed with methylene dichloride. The methylene dichloride was distilled under vacuum and 100 mL ethyl acetate was added at 40C to 45C and stirred for 15 minutes. The reaction mixture was heated to 75C and cooled to 10C to 15C. The reaction mixture was stirred for 2 hours and the precipitated product was filtered and washed with 150 mL ethyl acetate to obtain crystalline ethyl 3-(2-((4-cyanophenylamino)methyl)-l-methyl-N- (pyridin-2-yl)-lH-benzo[d]imidazole-5-carboxamido) propanoate of Formula (2B). The compound of Formula (2B) is characterized by x-ray powder diffraction as depicted in Fig.2. | ||
300 g | A mixture of 2-(4-cyanophenylamino)acetic acid (139 g) and tetrahydrofuran (750 ml) was heated to 50-55 C. A solution of N,N?-carbonyldiimidazole (177.6 g) in tetrahydrofuran (1000 ml) was added to the above reaction mixture at the same temperature over a period of 1 hour and stirred for 2 hours at 50-55 C. A solution of ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido) propanoate compound of formula-12 (250 g) in tetrahydrofuran (1500 ml) was added over a period of 2 hours at 50-55 C. and heated to 60-65 C. The reaction mixture was stirred for 50 hours at 60-65 C. After completion of the reaction, distilled off the solvent from the reaction mixture. Acetic acid was added to the reaction mixture and heated to 95-100 C. The reaction mixture was stirred for 5 hours at 95-100 C. Distilled off the solvent completely under the reduced pressure and the reaction mixture was cooled to 25-30 C. Water was added to the reaction mixture and the product was extracted with dichloromethane. Dichloromethane layer was washed with water followed by sodium chloride. Distilled off the solvent completely from the dichloromethane layer to obtain title compound. | |
127 g | A mixture of N-(4-cyanophenyl) glycine (56.6 g), CDI (61.6 g) and imidazole*HC1 (7.6g) in anhydrous EtOAc (1000 mL), was stirred for lh at 45-50C, under inert atmosphere. phenylene-l,2-diamine of formula 2 (lOOg) was, lot-wise, charged to the reaction mass. After stirring for another lh at the same temp, Glacial acetic acid (100mL) was added and the temperature of the reaction mass maintained at reflux for another6h. The reaction mixture cooled to 45-50C, and washed, successively with water and brine solution. The separated organic layer was concentrated under vacuum, till approx. 3 volumes were left behind. The reaction mass was cooled to room temp and 5% Brine solution (500 mL) was charged and the precipitate obtained was slurred for 3h. Theprecipitate was filtered, washed with EtOAc and dried under vacuum at 50C, to afford compound of formula 3 as off-white solid material (127.Og, 98.8% HPL pure). | |
77 g 2-(4-cyanophenylamino) acetic acid of Formula (E), 71.04 g CDI in 1000 mL Toluene were stirred at 25 C. to 35 C. The reaction mixture was heated to 55 C. to 60 C. and maintained for 2 hours. 100 g ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate of Formula (2A) was added to the reaction mixture and stirred for 3 hours at 60 C. to 65 C. The reaction mixture was further heated at 100 C. for 3 hours. Toluene was distilled under vacuum. The residue was treated with 500 mL methylene dichloride and organic layer was washed with water. The organic layer was filtered and washed with methylene dichloride. The methylene dichloride was distilled under vacuum and 100 mL ethyl acetate was added at 40 C. to 45 C. and stirred for 15 minutes. The reaction mixture was heated to 75 C. and cooled to 10 C. to 15 C. The reaction mixture was stirred for 2 hours and the precipitated product was filtered and washed with 150 mL ethyl acetate to obtain crystalline ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido) propanoate of Formula (2B). The compound of Formula (2B) is characterized by x-ray powder diffraction as depicted in FIG.2. | ||
1 kg of organic solvent a, 1.5 kg of SM2, and 1.2 kg of CDI were sequentially added to the reaction vessel, and the reaction was stirred at 10 to 50 C for 3 hours.Then, 1 kg of SM1 and 1 kg of organic solvent b were sequentially added, and the reaction was further stirred for 12 hours, and the solvent was distilled off under reduced pressure at 40 C to the reaction kettle.The acetic acid was put into the mixture, heated to 110 C for 5 hours, and the solvent was distilled off under reduced pressure at 100 C or less.Washing with water, recovering the solvent under reduced pressure in the organic phase, adding ethyl acetate to the residue, stirring to dissolve, and adding oxalic acidThe hydrate solution was stirred and crystallized at 22 C for 2 hours, centrifuged, and the filter cake was washed with ethyl acetate. The filter cake was dried under reduced pressure at 45 C for 6 hours.When, a pale yellow solid PR-I;Wherein, the solution of oxalic acid dihydrate is an ethanol solution containing oxalic acid dihydrate, and the oxalic acid dihydrate is in solution.The part by mass is 10%.Wherein, the organic solvent a and the organic solvent b are both N,N-dimethylformamide;Among them, the mass ratio of other materials is SM1: acetic acid = 1:8, SM1: dichloromethane = 1:3, dichloromethane: water =1:3, SM1: solution containing oxalic acid dihydrate = 1:5; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In propionic acid; at 130℃; for 12h; | A solution of ethyl 3- [N- (4-methylamino-3-aminobenzoyl) -N- (pyridin-2-yl) amino] propionate (1) (16.4 g, 0.048 mol ) Ethyl N- (4-cyanophenyl) aminoacetate (11) (11.8 g, 0.058 mol) and 300 mL of propionic acid, Stir for 1h, The temperature was raised to 130 C for 12 h. After cooling to room temperature, the reaction solution was poured into 1000 ml of sodium carbonate solution (10%) to precipitate a solid, filtered and the filter cake was washed three times with water to give crude III, which was recrystallized from ethyl acetate to give pure product (18.8 g, 81 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12.7 g | Step 1): CDI (7.80 g, 48.0 mmol) was slowly added to a solution of compound 1 (8.0 g, 45.7 mmol) in THF (150 mL) under an ice bath, and stirred at room temperature for 3 hours.After cooling to 0 C, compound 2 (14.0 g, 41.1 mmol) was added to the reaction system, and stirred at room temperature for 12 hours. After that, TBME (50 mL) was added, stirred for 10 minutes, filtered,Drying in vacuo gave a white solid. This solid was dissolved in acetic acid (100 mL), heated to 90 C, and stirred for 30 min.Concentrated under reduced pressure, added DCM (100 mL),Wash with a saturated aqueous sodium bicarbonate solution (20 mL × 3), concentrate the organic phase under reduced pressure, purify the residue with a silica gel column, and elute and concentrate with a gradient of petroleum ether / ethyl acetate = 100: 1 to 30: 1 to obtain a white solid product. Compound 3 (12.7 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10 - 35℃; | At 10-15 C, add the intermediate DGM1 (20g, 58mmol, 1.0eq), intermediate DGM2 (10.8g, 61mmol, 1.05eq) and 500mL dichloromethane to a 1000mL reaction flask, stir to dissolve, and then add EDCI ( 16.7g, 87mmol, 1.5eq), HOBt (11.7g, 87mmol, 1.5eq) and N, N-diisopropylethylamine (15g, 116mmol, 2eq),The temperature was raised to 30-35 C and the reaction was monitored by TLC. After the reaction,Add 200 mL of 10% acetic acid aqueous solution and 100 mL of dichloromethane, stir for 3 hours, let stand, and separate the organic phase. The organic phase is saturated aqueous sodium bicarbonate (200 mL × 1) and saturated aqueous sodium chloride (200 mL × 1) It was washed, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated under reduced pressure to obtain a crude solid. The crude product was recrystallized with 300 mL of ethanol to obtain 23.2 g of solid product DG1. Yield: 82%. |
Tags: 212322-56-0 synthesis path| 212322-56-0 SDS| 212322-56-0 COA| 212322-56-0 purity| 212322-56-0 application| 212322-56-0 NMR| 212322-56-0 COA| 212322-56-0 structure
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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: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
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. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
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. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
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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