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[ CAS No. 150322-43-3 ] {[proInfo.proName]}

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Chemical Structure| 150322-43-3
Chemical Structure| 150322-43-3
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Product Details of [ 150322-43-3 ]

CAS No. :150322-43-3 MDL No. :MFCD09954140
Formula : C20H20FNO3S Boiling Point : -
Linear Structure Formula :- InChI Key :DTGLZDAWLRGWQN-UHFFFAOYSA-N
M.W : 373.44 Pubchem ID :6918456
Synonyms :
PCR 4099;CS 747;LY640315
Chemical Name :5-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

Safety of [ 150322-43-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 150322-43-3 ]

* 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.

  • Downstream synthetic route of [ 150322-43-3 ]

[ 150322-43-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 204205-33-4 ]
  • [ 1151904-84-5 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
36.6% With triethylamine; In dichloromethane; at -15 - 20℃;Product distribution / selectivity; Example 3Synthesis of prasugrel by coupling thiophene acetate Al hydrochloride with the bromide CI2.00 g Thiophene acetate Al hydrochloride (Example 2) and 2.75 g bromide compound CI, were suspended in25 ml dichloromethane (dried over CaCl2). The suspension was cooled to -15/-10C,1.73 g triethylamine was added dropwise over 5 minutes. The yellow suspension was kept at -10C for 1 hour and was then allowed to slowly warm to 0-5C. Reaction progress was monitored with HPLC. After 4 hours 20 minutes, the reaction mixture was allowed to warm to ambient temperature. After 5.5 hours, the obtained dark brown suspension was washed with2x25 ml water, dried (Na2S04) and concentrated in vacuo.[0051] The obtained oil was filtered over silica 60 (63-200 mueta , 10 g) using toluene/ethyl acetate 20/1 (v/v) as eluens. The filtrate was concentrated in vacuo. To the obtained oil,20 ml isopropyl ether was added. The suspension was stirred over night at ambient temperature. The solid was isolated by filtration and dried at air.Isolated yield: 1.17 g (36.6%), off-white/bit yellowish solidHPLC: 98.4% purity
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 - 30℃; for 2 - 3h;Product distribution / selectivity; EXAMPLE 10: PREPARATION OF 2-ACETOXY-5-(A-CYCLOPROPYL CARBONYL-2-FLUOROBENZYL)-4,5,6,7-TETRAHYDROTHIENO[3,2- C]PYRIDINE (FORMULA I).Acetic acid 4,5,6,7-tetrahydro-thieno[3,2-c]pyhdin-2-yl ester hydrochloride (54.0 g), dichloromethane (750 mL) and diisopropylethylamine (94.6 mL) are charged into a round bottom flask. A solution of 2-fluoro-alpha-cyclopropylcarbonyl bromide (68.0 g of 2-fluoro-alpha-cyclopropylcarbonyl bromide in 250 mL of dichloromethane) is added to the reaction mixture dropwise at a temperature of 25 0C to 30 0C and maintained at that temperature for 2 to 3 hours. Water (500 mL) is added to the reaction mixture and layers are separated. Organic layer is washed with water (3*100 mL) and then dried over sodium sulfate followed by <n="45"/>evaporation under reduced pressure at a temperature of 35 0C to 45 0C. The resulting residue is subjected to silica gel column chromatography, using a 20:80 mixture of ethyl acetate and hexane by volume as the eluent, to give a yellow oil. Diisopropyl ether (200 ml_) is added to the obtained oil and stirred for 10 minutes at a temperature of 25 0C to 35 0C. The obtained suspension is filtered and the solid is dried at a temperature of 50 0C to 55 0C for 1 to 2 hours to afford the title compound (9.0 g).Purity: 74% by HPLC.
  • 2
  • [ 204205-33-4 ]
  • [ 1190589-93-5 ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
32.85% Example-6; Preparation of 2-Acetoxy-5-(alpha-cycloprpylcarbonyl-2-fluorobenzyl)-4,5,6,7- tetrahydrothieno [3,2-c] pyridine (I); To a solution of 2-acetoxy- -4,5,6,7-tetrahydrothieno[3,2-c]rhoyridine-p-toluenesulfonate (7.0 gm) in dimethylformamide (35 ml) was cooled to 5 -100C and was added with sodium bicarbonate (2.38 gm). The reaction mass was stirred for 15 minutes and added with 2- bromo-l-cyclopropyl-2-(2-fluorophenyl) ethanone (5.1 gm) in dimethylformamide (15 ml) and stirred for 5 hours at room temperature and followed by addition of acetic anhydride (3.8 ml) and stirred for 3 hrs at RT. After then reaction mass was cooled to 5 -10C and added with water (700 ml) and tert-butyl methyl ether (105 ml). Stirred the mixture at room temperature and filtered through celite bed. The celite bed was washed with TBME. The obtained TBME layer was washed with water and brine solution, dried the organic layer, and distilled solvent under reduced pressure to get the oily mass. The oily product was crystallized from ethanol to afford the good crystal of prasugrel free base, which was dried under vacuum at 50C for 24 hours (2.3 g, yield = 32.85%).
  • 3
  • [ 204205-33-4 ]
  • [ 115473-15-9 ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
Example-29: One pot process for the preparation of Prasugrel:A mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one hydrochloride (100 grams), potassium carbonate (215 grams) and acetonitrile (500 ml) was stirred for 30 minutes at 25-30C. 2-bromo-l-cyclopropyl-2-(2-fluorophenyl)ethanone (89.5 grams) in acetonitrile (50 ml) was added to the reaction mixture and stirred for 6 hours at 25-30C. The reaction mixture was filtered and removed the precipitated solid. Triethylamine (98.2 grams) was added to the filtrate and then cooled to 0-5C. Acetic anhydride (1 19 grams) was added to the reaction mixture and stirred for 30 minutes at 0-5C. The reaction mixture was stirred for 6 hours at 25-30C. Then the reaction mixture was quenched with water and extracted the reaction mixture into toluene. The solvent from the toluene layer was distilled off under reduced pressure and methanol (100 ml) was added to the obtained residue and stirred for 45 min at reflux temperature. The reaction mixture was cooled to 0-5C and stirred for 45 minutes. The obtained solid was filtered, washed with methanol and then dried to get the title compound.Yield: 60 grams; Purity by HPLC: 98.97%
Example-2 Preparation of 2-Acetoxy-5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (crude Prasugrel) 100 gm of 2-Oxo-2,4,5,6,7,7a-hexahydro thieno [3,2-c] pyridine hydrochloride was charged in 800 ml of dimethylformamide to obtain reaction mixture. To this sodium bicarbonate (175 gm) and alpha-Cyclopropyl carbonyl-2-fluorobenzylbromide (175 gm) was added at room temperature and allowed to heat at 50-55C for 2 hrs. The reaction mixture was cooled up to 10-15C. Acetic anhydride (118.67 gm) was added drop by drop at same temperature. The reaction mixture was heated to 40-45C for 3 hrs & cooled the reaction mixture to room temperature. Ethyl acetate and water was added to reaction mixture. The organic layer was separated and aqueous layer was discarded. The organic ethyl acetate layer was washed by aq. Na2CO3 followed by aq. NaCl solution. The ethyl layer was distilled of completely to obtain product mass. Methanol was charged in the obtained mass and stirred it at room temperature & cooled up to 0-5Cto obtain solid which was filtered and washed with methanol and dried at 50-55o C under vacuum to obtain crude prasugrel (85-95 gm).
  • 5
  • [ 204205-33-4 ]
  • [ 178688-49-8 ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
60.3% 68 ml of /V-ethyl-/V,/V-diisopropylamine (389 mmol; 2 eq.) are added to a suspension of 2-oxo-2,4, 5, 6,7a-hexahydrothieno[3,2-c]pyridine p-toluene sulfonate (66.86 g; 204.2 mmol; 1 .05 eq.) in 160 ml of acetonitrile. Thus prepared solution is added dropwise to a solution of 50 g of 1-cyclopropyl-2-bromo-2(2-fluorophenyl)ethanone (194.5 mmol) and 50 ml of acetonitrile, charged in a 1 L three-neck flask with a magnetic stirrer, thermometer and a dripping funnel closed with a calcium-chloride tube, such that the temperature does not exceed 30 C, and the mixture is stirred for 30 min, being monitored with TLC (silica gel on glass, toluene : ethyl acetate 3:1 ). After disappearance of the starting 1 -cyclopropyl-2-bromo-2(2-fluorophenyl)ethanone acetanhydride (60 ml; 3 eq.), A/-ethyl-A/,A/-diisopropylamine and a catalytic amount of /V,A/-dimethylaminopyridine are added to the mixture and reacted for 1 .5-2 h. The reaction is monitored with TLC in the same system. After this period the mixture is cooled down to -15 to -20 C and 150 ml of water are added in portions. The mixture is left to crystallize under thorough stirring at -15 to -6 C for 1 .5 to 2 hours. The separated product - prasugrel base - is aspirated and washed with 2 chi 25 ml of cooled ethanol on fritted glass and dried freely in air. 43.79 g (60.3 %) of crude prasugrel base with the purity of 99.44% (HPLC) is obtained; the content of the compound of formula II lower than 0.05%.The crude product obtained in this manner (43 g) is dissolved in acetonitrile (480 ml), acetanhydride (8 ml) is added and, after stirring for 1 hour, cooled down to -15 C, 200 ml of water are added in portions and the product is left to crystallize at -12 to -6 C for two hours. By aspiration on fritted glass, washing with 2x25 ml of cooled ethanol and drying in air, 34.81 g of white crystals with the purity of 99.4% (HPLC) are obtained; the content of the compound of formula II lower than 0.05%.
  • 6
  • [ 204205-33-4 ]
  • [ 951380-43-1 ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
29% V-Ethyldiisopropylamine (1.7 ml; 9.7 mmol) is added to a suspension of 2-oxo- 2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride (0.89 g; 4.6 mmol) in acetonitrile (4 ml). Thus prepared solution is added dropwise to a solution of 1- cyclopropyl-2-bromo-2(2-fluorophenyl)ethanone (1.13 g; 4.4 mmol) in acetonitrile (2 ml) and the reaction is stirred at the room temperature for 1 .5 hours. Subsequently, acetanhydride (1 .2 ml; 13.2 mmol), /V-ethyldiisopropylamine (0.6 ml; 3.5 mmol) and a catalytic amount of N,A/-dimethylaminopyridine are added to the solution. The reaction is stirred at the room temperature for 2 hours. Then, the reaction mixture is cooled down to -15 C, 2.5 ml of water are added and the reaction is stirred at -12 to -8 C for 2 hours. The resulting white crystals are aspirated, washed with ethanol and dried in air. 0.48 g of prasugrel base (29%) is obtained. Melting point: 1 17.5-1 19.5 C, HPLC: purity 98.5%; content of the compound of formula II 0.09%.The crude product obtained in this manner (0.45 g) is dissolved in acetonitrile (10.5 ml) and, after addition of 0.2 ml of acetanhydride, the mixture is stirred at the room temperature for 1 h. Then, the mixture is cooled down to -15 C, water (4 ml) is added and white crystals precipitate under stirring at the temperature of -2 to -8 C. After two hours they are aspirated, washed with ethanol and dried. 0,31 g of white crystals of prasugrel are obtained. Melting point: 120 -121 C. HPLC: purity 99.4%; content of the compound of formula II 0.07%.
  • 7
  • [ 204205-33-4 ]
  • [ 952340-39-5 ]
  • [ 150322-43-3 ]
  • 9
  • [ 204205-33-4 ]
  • [ 952340-39-5 ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
55% Example 82-Acetoxy-5-(2-fluoro-a-cyclopropyl-carbonyI-benzyl)-4,5,6,7- tetrahydro-4H-thieno[3,2-c] pyridine (prasugrel, compound of theFormula (I))65.5 g (0.2 mol) of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridine-2- one joara-toluenesulfonate (compound of the Formul (II), HA=PTSA) and 160 ml of N,N-dimethylformamide are combined. To this mixture are added 75.3 cm (56.9 g; 0.44 mol) NN-diisopropylethylamine (DIPEA). Subsequently while cooling the reaction mixture on an ice/water bath, 53.8 g of 2-bromo-l-cyclopropyl-2-(2-fmorophenyl)- ethanone of the Formula (III) having 95.5% content according to gas chromatographic assay, dissolved in 94 ml (88.7 g) of Nu,Nu- dimethylformamide are added dropwise in 30 minutes and the thus obtained mixture is stirred for one hour at room temperature. Thereafter 37.65 cm3 (28.43 g; 0.22 mol) of DIPEA are added to the reaction mixture and while stirring intensively and maintaining the temperature between 15 and 20 C, 28.4 ml (30.6 g; 0.30 mol) of acetic anhydride are added dropwise. Addition of acetic anhydride is followed by stirring for one hour at room temperature. The reaction mixture is poured into a mixture of ice, water and ethylacetate. The layers are separated, the aqueous layer is washed with ethylacetate.The organic layer and the washings are combined and dried over magnesium sulfate. The solution is evaporated in vacuo, and ethanol is added to the residue. The mixture is cooled to a temperature between 0 and 5 C, the crystals are filtered and washed with ethanol.Thus 44.7 g (60.0 %) of raw prasugrel are obtained, which are recrystallized from ethanol.Yield, 41.1 g (55.0 %) colourless, crystalline solid.Assay (measured by high-performance liquid chromatography), better than 99.80 %.The individual concentration of the impurities of the Formulae(XXIV) and (XXIVa) is less than 25 ppm each.Total yield (calculated for 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine hydrochloride of the Formula (IX)), 45.7 %.Melting point, 120-121 CIR (KBr, cm-1): 3388, 2920, 2767, 1758, 1704, 1586, 1488, 1369, 1217, 1194, 1127, 1011.1H-NMR (CDC13, 500 MHz): 7,47 (1H, td, J=7,5; 1,8 Hz); 7,30 (1H, m); 7,16 (1H, td, J=7,5; 1,1 Hz); 7,10 (1H, td, J=8,2; 1,1 Hz); 6,26 (1H, s); 4,82 (1H, s); 3,56 (1H, d, J=14,3 Hz); 3,48 (1H, d, J-14,3 Hz); 2,90 (1H, m); 2,78 (3H, m); 2,28 (1H, m); 2,23 (3H, s); 1,05 (1H, m); 1,00 (1H, m); 0,84 (2H, m).13C-NMR (CDCI3, 125 MHz): 207,4; 167,5; 161,1; 149,4; 130,4; 129,7; 129,3; 125,6; 124,2; 122,0; 115,6; 112,8; 71,5; 50,3; 48,3, 24,9; 20,4; 18,1, 11,8, 1 1,3. Elemental analysis calculated for the Formula C20H20FNO3S (M: 373,45)Calculated: C 64.33; H 5.40; N 3.75; S 8.59 %.Measured: C 64.18; H 5.50; N 3.69; S 8.75 %.
55% Example 4 Preparation of 2-Acetoxi-5-(2-fluor-alpha-cyclopropyl-carbonyl-benzyl)-4,5,6,7-tetrahydro-4H-tieno[3,2-c]pyridine (prasugrel, I) 160 cm3 of DMF are added to 65.5 g (0.2 mol) of 5,6,7,7a-tetrahydro-4H-tieno[3,2-c]-pyridine-2-on para-toluenesulfonate (II, HA=PTSA). 75.3 cm3 (56.9 g; 0.44 mol) of N,N-diisopropyl-ethyl-amine (DIPEA) are added to the solution and 55.4 g of 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)-ethanon (III) (containing 92.8% of GC) dissolved is 94 cm3 (88.7 g) of dimethyl-formamide is added dropwise within app. 30 minutes under ice water cooling. The mixture is stirred for 1 hour at room temperature. 37.65 cm3 (28.43 g; 0.22 mol) of DIPEA are added to the reaction mixture and under intensive stirring 28.4 cm3 (30.6 g; 0.30 mol) of acetic acid anhydride are added dropwise. The mixture is stirred for 1 hour at room temperature. The reaction mixture is poured onto the mixture of ice water and ethylacetate. The phases are separated and the aqueous phase is extracted with ethylacetate. The collected organic phases are dried on MgSO4. The solvent is removed in vacuo and ethanol is added to the remaining product. After cooling to 0-5 C. the precipitated crystals are filtered, washed with ethanol. The yield is 44.7 g (60.0%) crude prasugrel base.Yield: 41.1 g (55.0%) colorless, crystalline product, HPLC purity >99.80%.[0068]Yield for the whole synthetic process, calculated on the 4,5,6,7-tetrahydro-tieno[3,2-c]pyridine hydrochloride of the formula (VII) is 45.7%.[0069]Mp.: 120-121 C.[0070]IR (KBr, cm-1): 3388, 2920, 2767, 1758, 1704, 1586, 1488, 1369, 1217, 1194, 1127, 1011.[0071]1H-NMR (CDCl3, 500 MHz): 7.47 (1H, td, J=7.5; 1.8 Hz); 7.30 (1H, m); 7.16 (1H, td, J=7.5; 1.1 Hz); 7.10 (1H, td, J=8.2; 1.1 Hz); 6.26 (1H, s); 4.82 (1H, s); 3.56 (1H, d, J=14.3 Hz); 3.48 (1H, d, J=14.3 Hz); 2.90 (1H, m); 2.78 (3H, m); 2.28 (1H, m); 2.23 (3H, s); 1.05 (1H, m); 1.00 (1H, m); 0.84 (2H, m).[0072]13C-NMR (CDCl3, 125 MHz): 207.4; 167.5; 161.1; 149.4; 130.4; 129.7; 129.3; 125.6; 124.2; 122.0; 115.6; 112.8; 71.5; 50.3; 48.3, 24.9; 20.4; 18.1, 11.8, 11.3.[0073]Elementary analysis [calculated on the basis of the formula of C20H20FNO3S (M: 373.45)][0074]Calculated: C 64.33; H 5.40; N 3.75; S 8.59.[0075]Measured: C 64.18; H 5.50; N 3.69; S 8.75.
55% A mixture is prepared from 65.5 g (0.2 mole) of 5,6,7,7a-tetrahydro-4H-thieno-[3,2-c]pyridine- 2-one (compound of the Formula (8)) p-toluenesulfonate and 160 ml of dimethyl formamide. 75.3 ml (56.9 g, 0.44 mole) of Nu,Nu-diisopropyl-ethylamine /DIPEA/ are added, whereupon 53.8 g of 2-bromo-l-cyclopropyl-2-(2-fluorophenyl)-ethanone (GC content 95.5 %), compound of the Formula (7, X = Br) dissolved in 94 ml (88.7 g) of dimethyl formamide are added under cooling with ice-cold water within about 30 minutes. The reaction mixture is stirred at room temperature for an hour, whereupon 37.65 ml (28.43 g, 0.22 mole) of DIPEA are added and thereafter 28.4 ml (30.6 g, 0.30 mole) of acetic anhydride are added drop wise at 15-20C under intensive stirring. The reaction mixture is stirred at room temperature for a further hour, whereupon the reaction mixture is poured on a mixture of ice-cold water and ethyl acetate. The phases are separated and the aqueous layer is extracted with ethyl acetate. The united organic layers are dried over magnesium sulphate. The solvent is removed in vacuo. To the evaporation residue ethanol is added, the mixture is cooled to 0-5C, the crystals obtained are filtered and washed with ethanol. The crude prasugrel is recrystallized from ethanol. Thus 41.1 g /55.0 %/ of a colourless crystalline product are obtained. HPLC purity larger than 99.80 %. Mp: 120-121C.
  • 10
  • [ 204205-33-4 ]
  • [ 115473-15-9 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
Example 29One Pot Process for the Preparation of PrasugrelA mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one hydrochloride (100 grams), potassium carbonate (215 grams) and acetonitrile (500 ml) was stirred for 30 minutes at 25-30 C. <strong>[204205-33-4]2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone</strong> (89.5 grams) in acetonitrile (50 ml) was added to the reaction mixture and stirred for 6 hours at 25-30 C. The reaction mixture was filtered and removed the precipitated solid. Triethylamine (98.2 grams) was added to the filtrate and then cooled to 0-5 C. Acetic anhydride (119 grams) was added to the reaction mixture and stirred for 30 minutes at 0-5 C. The reaction mixture was stirred for 6 hours at 25-30 C. Then the reaction mixture was quenched with water and extracted the reaction mixture into toluene. The solvent from the toluene layer was distilled off under reduced pressure and methanol (100 ml) was added to the obtained residue and stirred for 45 min at reflux temperature. The reaction mixture was cooled to 0-5 C. and stirred for 45 minutes. The obtained solid was filtered, washed with methanol and then dried to get the title compound.Yield: 60 grams; Purity by HPLC: 98.97%
  • 11
  • [ 204205-33-4 ]
  • 2-trimethylsilyloxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]
  • [ 108-24-7 ]
  • [ 150322-43-3 ]
YieldReaction ConditionsOperation in experiment
The product obtained in Example 3 was added to 5000 ml of methylene chloride, 1400 ml of TEA and 80 g of tetrabutylammonium bromide,A-bromo-o-fluorobenzyl cyclopropyl ketone (1100-1200 g) was added dropwise. After completion of the dropwise addition, the mixture was heated under reflux and stirring was continued for 3 hours,TLC detection reaction was complete, add 4-dimethylaminopyridine (DMAP) 25g,Triethylamine (1000 ml) was dropwise added, and acetic anhydride (750 ml) was added thereto. The mixture was reacted at room temperature and the reaction was complete by TLC, add water and extracted with dichloromethane, washed with saturated sodium bicarbonate, and concentrated to give an oil, the crystallization to obtain prasugrel as a white solid.
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