Structure of 952340-39-5
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 952340-39-5 |
Formula : | C14H17NO4S2 |
M.W : | 327.42 |
SMILES Code : | O=C1C=C2CNCCC2S1.O=S(C3=CC=C(C)C=C3)(O)=O |
MDL No. : | MFCD12407185 |
* 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 |
---|---|---|
With sodium carbonate; In N,N-dimethyl-formamide; at 0 - 5℃; for 3h;Product distribution / selectivity; | Example-18: Preparation of 5-(alpha-cyclopropyIcarbonyl-2-fluorobenzyI)-2-oxo- 2,4,5,6,7,7a-hexahydrothieno[3, 2-c] pyridine.; 2-fluoro-alpha-cyclopropyl carbonyl benzyl bromide (3.5 grams) was added to a mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one p-touenesulfonate (5.0 grams) and sodium carbonate (3.5 grams) in dimethylformamide (80 ml) at 0-50C and stirred for 3 hours. The reaction mixture was quenched with water and then extracted it with methylene chloride. The methylene chloride washed with <n="21"/>water and organic and aqueous layers were separated. The methylene chloride from the organic layers was distilled off completely and the obtained residue purified using cyclohexane and ethyl acetate to provide the title compound. Yield: 1.4 grams | |
With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 5℃; for 3h;Product distribution / selectivity; | Example-21: Preparation of 5-(alpha-cyclopropyIcarbonyl-2-fluorobenzyl)-2-oxo- 2,4,5,6,7,7a-hexahydrothieno[3, 2-c] pyridine.;The title compound is prepared analogues manner to example- 18 using potassium carbonate in place of sodium carbonate Yield: 1.9 grams | |
With potassium carbonate; In acetonitrile; at 0 - 5℃; for 3h;Product distribution / selectivity; | Example-20: Preparation of 5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo- 2,4,5,6,7,7a-hexahydrothieno[3, 2-c] pyridine.; The title compound is prepared analogues manner to example- 18 using potassium carbonate as a base and acetonitrile as a solvent in place of sodium carbonate and dimethylformamide. Yield: 1.5 grams |
Example-35: Preparation of 5-(a-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo- 2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine compound of formula-7:A mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one-p-toluene sulfonate (100 grams), potassium carbonate (63.5 grams) and acetonitrile (1000 ml) was stirred for 30 minutes at 25-30C. 2-bromo-l-cyclopropyl-2-(2-fluorophenyl) ethanone (66 grams) prepared as per example-34 in acetonitrile (30 ml) was added to the reaction mixture and stirred for 7 hours at 25-30C. The reaction mixture was filtered and removed the precipitated solid. The filtrate was distilled off completely under reduced pressure, ethyl acetate followed by cyclohexane was added to it. The reaction mixture was stirred for 25 minutes at 40-45C. The reaction mixture was cooled to 25-30C and stirred for an hour. The reaction mixture was filtered and solvent form the filtrated was distilled off completely under reduced pressure to get the title compound.Yield: 70 grams | ||
With potassium carbonate; In acetonitrile; at 25 - 30℃; for 7.5h; | Example 35 Preparation of 5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine compound of formula-7 A mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one-p-toluene sulfonate (100 grams), potassium carbonate (63.5 grams) and acetonitrile (1000 ml) was stirred for 30 minutes at 25-30 C. 2-bromo-1-cyclopropyl-2-(2-fluorophenyl) ethanone (66 grams) prepared as per example-34 in acetonitrile (30 ml) was added to the reaction mixture and stirred for 7 hours at 25-30 C. | |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1.5h; | To a mixture of 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), PTSA salt) and 150 ml of dimethyl formamide 75.3 ml (56.9 g, 0.44 mole) of Nu,Nu-diisopropyl-ethyl amine /DIPEA/ are added, whereupon a solution of 55.4 g 2-bromo-l-cyclopropyl-2-(2-fluoro-phenyl)-ethanone (compound of the Formula (7)), GC content 92.8 %/ in dimethyl formamide is added drop wise during about 30 minutes. The reaction mixture is stirred at room temperature for an hour, and then poured onto a mixture of ice-cold water and ethyl acetate. The phases are separated; the aqueous layer is extracted with ethyl acetate. The united organic layers are dried over magnesium sulphate and the solvent is removed in vacuo. The product thus obtained can be directly used for the preparation of prasugrel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example-20: Preparation of 5-(a-cycIopropyIcarbonyl-2-fIuorobenzyl)-2-oxo- 2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrobromide:A mixture of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one-p-toluene sulfonate (100 grams), potassium carbonate (63.5 grams) and acetonitrile (1000 ml) was stirred for 30 minutes at 25-30C. 2-bromo-l-cyclopropyl-2-(2-fluorophenyl) ethanone (66 grams) in acetonitrile (30 ml) was added to the reaction mixture and stirred for 7 hours at 25-30C. The reaction mixture was filtered and removed the precipitated solid. The filtrate was distilled off completely under reduced pressure; ethyl acetate followed by cyclohexane was added to it. The reaction mixture was stirred for 25 minutes at 40-45C. The reaction mixture was cooled to 25-30C and stirred for an hour. The reaction mixture was filtered and solvent from the filtrate was distilled off completely under reduced pressure. 250 ml of acetone was added to the obtained compound and cooled the reaction mixture to 0-5C. Aqueous hydro bromide (70 ml) was slowly added to the reaction mixture. Raised the temperature to 20-25 C and stirred for 6 hrs at same temperature. Cooled the reaction mixture to 0-5C and stirred for 2 hrs at same temperature. Filtered the precipitated solid and washed with acetone to get the title compound.Yield: 85 gms. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1.5h;Cooling with ice; | Example 4Preparation of 2-Acetoxi-5-(2-fluor-a-cyclopropyl-carbonyl-benzyl)-4,5,6,7- tetrahydro-4i/-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 /? ra-toluenesulfonate (II, HA=PTSA). 75,3 cm3 (56,9 g; 0,44 mol) of NiV-diisopropyl-ethyl-amine (DIPEA) are added to the solution and 55,4 g of 2-bromo-l-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 cm (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 MgS04. 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. The crude product is recrystallized from 5 fold volume ethanol.Yield: 41,1 g (55,0 %) colorless, crystalline product, HPLC purity > 99,80 %. 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 %.Mp.: 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 (IH, td, J=7,5; 1,8 Hz); 7,30 (IH, m); 7,16 (IH, td, J=7,5; 1,1 Hz); 7,10 (IH, td, J=8,2; 1,1 Hz); 6,26 (IH, s); 4,82 (IH, s); 3,56 (IH, d, J=14,3 Hz); 3,48 (IH, d, J=14,3 Hz); 2,90 (IH, m); 2,78 (3H, m); 2,28 (IH, m); 2,23 (3H, s); 1,05 (IH, m); 1,00 (IH, 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, 11,3. Elementary analysis [calculated on the basis of the formula of C20H2oFN03S (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. | |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Cooling with ice; | Example 5Preparation of 2-Acetoxy-5-(2-fluor-a-cyclopropyl-carbonyl-benzyI)-4,5,6,7- tetrahydro-4J3r-tieno[3,2-c] pyridine (prasugrel, I)1st step: 150 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 ^ara-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-l-cyclopropyl-2-(2-fluorophenyl)-ethanon (III) (containing 92,8 % of GC) dissolved in 94 cm3 (88,7 g) of dimethyl-formamide are added dropwise within app. 30 minutes under ice water cooling. The mixture is stirred for 1 hour at room temperature. The reaction mixture is poured onto the mixture of ice water and ethyl acetate. The phases are separated and the aqueous phase is extracted with ethyl acetate. The collected organic phases are dried on MgS04. The solvent is removed in vacuo. |
Yield | Reaction Conditions | Operation 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. |