Structure of 120069-21-8
*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. : | 120069-21-8 |
Formula : | C5H9NO2S |
M.W : | 147.20 |
SMILES Code : | N#CCS(=O)(C(C)C)=O |
MDL No. : | MFCD00051755 |
InChI Key : | FJZQCBCJTUWIOQ-UHFFFAOYSA-N |
Pubchem ID : | 2778530 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 34.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.67 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.41 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.02 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.74 |
Solubility | 26.8 mg/ml ; 0.182 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.14 |
Solubility | 10.6 mg/ml ; 0.0723 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.1 |
Solubility | 11.7 mg/ml ; 0.0798 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.06 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.54 |
* 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 dimethylsulfide borane complex; In tetrahydrofuran; for 0.666667h;Heating / reflux; | Iso-Propylsulfonylethylamine Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in MeOH) was added to the reaction slowly due to gas evolution. The volatiles were removed and frexh methanol was added to the resulting residue. Again, the volatiles were removed and the resulting residue was taken up in CH2Cl2 (25 mL) and washed with saturated potassium carbonate (aqueous). The organic layer was dried over sodium sulfate and the volatiles were removed to afford the title compound. GC-MS m/z 152 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylether-borane complex; In tetrahydrofuran; for 0.666667h;Heating / reflux; | Iso-Propylsulfonylethylamine Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in MeOH) was added to the reaction slowly due to gas evolution. The volatiles were removed and frexh methanol was added to the resulting residue. Again, the volatiles were removed and the resulting residue was taken up in CH2Cl2 (25 mL) and washed with saturated potassium carbonate (aqueous). The organic layer was dried over sodium sulfate and the volatiles were removed to afford the title compound. GC-MS m/z 152 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.40 g (99%) | With potassium carbonate; In dichloromethane; acetone; | 1 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile A solution of 2-propanesulfonylacetonitrile (2.0 g, 13.6 mmol) in dry acetone (25 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-methoxyphenyl isothiocyanate (2.36 g, 14.3 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (2.54 ml, 40.8 mmol) was added to the filtrate, and stirring was continued for 60 h. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 4.40 g (99%) of the title compound as yellow crystals. Mp 107-110 C. 1H NMR (200 MHz, CDCl3): delta=1.44 (d, 6H), 2.22 (s, 3H), 3.36 (heptet, 1H), 3.83 (s, 3H), 6.81 (m, 1H), 6.85 (dd, 1H), 6.87 (dd, 1H), 7.32 (dd, 1H), 9.91 (br s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.65 g (99%) | With potassium carbonate; In dichloromethane; acetone; | 1 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile A solution of <strong>[120069-21-8]2-propanesulphonylacetonitrile</strong> (4.0 g, 27.2 mmol) in dry acetone (50 ml) was stirred while dry potassium carbonate (7.52 g, 54.4 mmol) and 3,5-bis(trifluoromethyl)phenyl isothiocyanate (7.72 g, 4.87 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (5.08 ml, 81.6 mmol) was added to the filtrate, and stirring was continued for 48 h. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 11.65 g (99%) of the title compound as yellowish brown crystals. Mp 130-133 C. 1H NMR (200 MHz, CDCl3): delta=1.47 (d, 6H), 2.35 (s, 3H), 3.44 (heptet, 1H), 7.73 (s, 2H), 7.80 (s, 1H), 10.10 (br s, 1H); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; dimethyl sulfoxide; | a) (1-Methylethylsulfonyl)phenylacetonitrile A mixture of iodobenzene (13.9g, 68mmol), <strong>[120069-21-8](1-methylethylsulfonyl)acetonitrile</strong> (20.0g, 136mmol), copper (I)iodide (1.29g, 6.8mmol) and potassium carbonate (37.6g, 272mmol) in dimethylsulfoxide (100mL) was stirred at 120 C under an atmosphere of nitrogen for 40h. The dark blue mixture was allowed to cool to room temperature, poured into 2M hydrochloric acid (300mL) and extracted with ether (200mL) and ethyl acetate (2 x 150mL). The combined organic extracts were washed with water (8 x 125mL), dried (MgSO4), filtered and evaporated in vacuoto yield a black oil. This was dissolved in dichloromethane and filtered through a large pad of 'flash' silica, eluding with dichloromethane. Fractions containing the product were combined and concentrated, yielding a yellow oil. This was distilled in a short-path distillation apparatus, providing a yellow oil (B.Pt. 230 C at 0.3 mBar). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; dimethyl sulfoxide; | PREPARATION 18 Preparation of (propane-2-sulfonyl)phenylacetonitrile A mixture of iodobenzene (13.9g, 68mmol), propane-2-sulfonylacetonitrile (20.0g, 18mmol), copper (I) iodide (1.29g, 6.8mmol) and potassium carbonate (37.6g, 272mmol) in DMSO (100mL) was stirred at 120 C under an atmosphere of nitrogen for forty hours. The dark blue mixture was allowed to cool to room temperature, poured into dilute hydrochloric acid (300mL) and extracted with ether (200mL) and ethyl acetate (2 x 150mL). The combined organic extracts were washed with water (8 x 125mL), dried (MgSO4), filtered and evaporated in vacuoto yield a black oil (20g). This was dissolved in dichloromethane and filtered through a large pad of 'flash' silica, eluding with dichloromethane. Fractions containing the product were combined and concentrated, yielding a yellow oil. This was distilled in a short-path distillation apparatus, providing a yellow oil (B.Pt. 230 C at 0.3 mBar). Also prepared in this fashion starting from methanesulfonylacetonitrile was methanesulfonyl phenylacetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Step A: The title compound was prepared from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and propane-2-sulphonylacetonitrile in 34% yield 1H NMR (DMSO-d6): delta ppm 1.32 (d, J=6.78 Hz, 6 H) 1.41 (s, 18 H) 3.56 (m, 1 H) 7.98 (s, 2 H) 8.16 (s, 1 H) 8.41 (s, 1 H); HPLC-MS (Method A): m/z=464 (M+1); Rt=5.0 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tetrabutylammomium bromide; at 100℃; for 0.5h; | 66.6 g (0.5 mol) of isopropyl cyanoethyl sulfone, 4.0 g of tetrabutylammonium bromide and 50 mL of deionized water were added to the hydrothermal reactor,Further, 50 mL (0.4 mol) of 3-diethylaminoacrolein was added,Mixed evenly, at a certain 100 reaction for about 0.5h,TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimation iodine color) 3-diethylamino acrolein reaction is complete, the reaction solution by adding 10% sodium hydroxide lye to adjust the pH to neutral,Ethyl acetate solvent 100mL × 3 times extraction, the organic phase washed with water, anhydrous sodium sulfate for 6h,Distilled off the solvent ethyl acetate (recovered) to give 97.5 g of a light brown oil in a yield of 98.0%.The product was characterized by HR-MS, i.e., 2-isopropylsulfonyl-5- (N, N-diethyl) amino-2,4-pentadienenitrile. |
95.1% | With sodium isopropylate; at 80℃;Sonication; | In a 500 mL three-necked round bottom flask,50 mL (0.4 mol) of 3-diethylaminoacrolein was added,10 mL of sodium isopropoxide and 66.6 g (0.5 mol) of isopropyl cyanoethyl ethyl sulfone,Mix well, the prepared reactor into the ultrasonic instrument,Set the ultrasonic radiation conditions, at a temperature of 80 ,Ultrasonic power of 300W and the frequency of 80KHz reaction conditions, TLC test Measured (petroleum ether: dichloromethane 1: 2 expansion, sublimation of iodine color) 3 - diethylamino acrolein reaction was complete, add deionized water 10mLIn addition to impurities, organic solvents were distilled off to give 97.5g of light brown oil, yield 95.1% |
93.2% | With piperidine; at 120℃; for 0.2h;Microwave irradiation; Green chemistry; | In a 500 mL three-necked flask equipped with a thermometer, 73 mL (0.6 mol) of isopropyl cyanoethylsulfone and 10 mL of piperidine were added followed by 62 mL (0.5 mol) of 3-diethylaminoprop-2-enal, mixed evenly, the prepared reactor into the microwave instrument, set the microwave radiation conditions. The reaction was carried out at a temperature of 120 C, a microwave power of 350 W and a frequency of 2450 MHz. TLC detection (petroleum ether: dichloromethane 1: 2 developed, sublimation iodine color) 3-diethylaminov reaction is complete, the reaction time 0.2h, adding potassium carbonate solution to adjust the pH = 7-8,The aqueous layer was extracted with methylene chloride 100mL x 3 times. The organic layers were combined and dried over anhydrous Na2SO4. The organic phase was recovered from the dichloromethane and evaporated to give 119.5 g of a pale brown oil in a yield of 93.2%. |
92.2% | With N-ethyl-N-ethylpiperidinium chloride; at 63℃; for 6h; | 61 mL (0.5 mol) of isopropyl cyanoethyl sulfone and 50 mL of N-ethyl-N-ethylpiperidine chloride were added to the reactor, and 3-bis Ethylacrolein 62mL (0.5mol), mixed, heated to 63 temperature and incubated for 6h reaction, TLC (stone Ether: dichloromethane 1: 2 expand, sublimation of iodine color) 3-diethylamino acrolein reaction was complete, cooled to room temperature, the organic solvent Toluene 60mL extracted three times, the remaining ionic liquid water washing, vacuum drying repeatedly used, the organic phase was distilled off under reduced pressure solvent toluene recovery, 118.2 g of a pale brown oil was obtained in a yield of 92.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammomium bromide; at 40℃;Microwave irradiation; Green chemistry; | In a 500 mL three-necked flask reactor equipped with a thermometer, 73.6 g (0.5 mol) of isopropyl cyanoethylsulfone, 10 mL of tetrabutylammonium bromide, and 3-dimethylaminoprop-2-enal 62 mL (0.5 mol) were mixed and homogenized. The prepared reactor was placed in a microwave oven. The reaction was carried out under the conditions of microwave irradiation, 40 C temperature, microwave power of 100W and the frequency of 2450MHz under the conditions of the reaction,TLC detection (petroleum ether: dichloromethane 1: 2 expansion, sublimation iodine color) 3-dimethylaminoprop-2-enal was completely reacted to prepare an intermediate. Cooled to room temperature, passed HCl gas, reacted at room temperature, and the reaction was followed by HPLC until the reaction was complete and the reaction time was 1 h. Add 5% potassium hydroxide solution to adjust the pH = 7-8, separated, the water layer with dichloromethane 100mL × 3 times extraction, combined organic layer. After washing with water, the molecular sieves were dried and filtered and the solvent was distilled off. The dichloromethane was recovered to give 2-chloro-3-isopropylsulfonylpyridine, 101.0 g of a colorless liquid in a yield of 92.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylhexadecylammonium chloride; In water; at 60℃; | A 500 mL three-necked flask equipped with a thermometer was charged with 69 mL (0.5 mol) of N, N-dibutylaminopropenal, 2.0 g of triethylhexadecylammonium chloride and 100 mL of deionized water, 14.8 g (0.5 mol) of cyanoethylsulfone, homogeneously, reacted at a temperature of 60 C, TLC (petroleum ether: methylene chloride 1: 2 developed, sublimed iodine) N, N-dibutyl The allyl aldehyde reaction was complete and then cooled to 25 C, followed by passing of HCl gas, followed by the HPLC until the reaction was complete.After the completion of the reaction, the sodium carbonate solution was added to adjust the pH to 7-8, and the aqueous layer was extracted with 100 mL of ethyl acetate. The organic layers were combined and washed with 10 mL of deionized water. The organic layer was dried overnight, The compound 5 (structural formula is shown in Table 1), namely 2-chloro-3-isopropylsulfonylpyridine and 101.6 g as a colorless liquid, in a yield of 92.5%, was obtaine 92.5%, was obtained by filtration and heating to remove the solvent. | |
With triethylhexadecylammonium chloride; In water; at 60℃; | In a 500 mL three-necked flask equipped with a thermometer, 69 mL (0.5 mol) of 3- (N, N-dibutyl) aminopropenal, 2.0 g of triethylhexadecylammonium chloride and 100 mL of deionized water were added,Then, 73.6 g (0.5 mol) of isopropyl cyanoethylsulfone was added and the mixture was homogeneously reacted at a temperature of 60 C,TLC detection (petroleum ether: dichloromethane 1: 2 expansion, sublimed iodine color) 3- (N, N-dibutyl) amino acrolein reaction is complete,Cooled to 10 C, HCl gas was passed at 10 C, and the reaction was followed by HPLC until the reaction was completed.After the completion of the reaction, the sodium carbonate solution was added to adjust the pH to 7-8, and the aqueous layer was extracted with 100 mL of ethyl acetate. The organic layers were combined, washed with 10 mL of deionized water,The organic layer of molecular sieves were dried overnight, filtered, heated and evaporated to remove the solvent,2-chloro-3-isopropylsulfonylpyridine, 101.6 g of colorless liquid in a yield of 92.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | The reactor was charged with 73.6 g (0.5 mol) of isopropyl cyanoethyl ethyl sulfone, 50 mL of tetrabutylphosphine bromide,3-dimethylaminoacrolein 62mL (0.5mol), mixed well,Microwave heating to 140 C and incubated for 20min reaction, TLC detection (petroleum ether: dichloromethane 1: 2 expansion, sublimation of iodine color) 3 - dimethylaminoacrolein reaction was complete, cooled to 10 C, the organic solvent ether 60mL Extraction 3 times, I phase ionic liquid washing, reuse after vacuum drying, the organic phase was dried HCl gas, HPLCThe reaction is followed until the reaction is complete. Join mass fraction of 20% sodium hydroxide solution to adjust the pH = 7-8, liquid separation, aqueous layer with B. Ether 100mL × 3, the organic layer was combined, washed with water, liquid separation, molecular sieve drying, filtration, the solvent was evaporated under reduced pressure diethyl ether recovery, There was 2-chloro-3-isopropylsulfonylpyridine as a colorless liquid, 101.6 g, yield 92.5%. The product was characterized by HR-MS as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; at 60℃;Sonication; | In a 500 mL three-necked flask equipped with a thermometer,First, 69 mL (0.5 mol) of 3-bis (n-propyl) aminoacrolein and 5.0 g of K2CO3 were added, followed by adding 73.6 g (0.5 mol) of isopropyl cyanoethyl sulfone,well mixed,The prepared reactor into the ultrasonic instrument, set the ultrasonic radiation conditions,At a temperature of 60 C,Ultrasonic power of 300W and the frequency of 100KHz reaction conditions,TLC (petroleum ether: dichloromethane 1: 2 developed, sublimation of iodine color) 3-bis (n-propyl) amino acrolein reaction was complete, cooled to 20 C, HCl gas was introduced,The conditions of ultrasonic irradiation were the same as above, the reaction temperature was 20 C,After about 50 min of reaction, HPLC traces the reaction until the reaction is complete. Then after the reaction, sodium carbonate solution was added to adjust pH = 7-8,The organic phase was washed with 10 mL of deionized water and then separated. The organic layer was dried over molecular sieves overnight, filtered, the solvent removed by heating and evaporation to give 2-chloro-3- Isopropylsulfonylpyridine, 101.3 g of a colorless liquid in a yield of 92.2%. |
A176859 [104458-24-4]
2-(Methylsulfonyl)ethanamine hydrochloride
Similarity: 0.55
A672347 [7484-34-6]
2,2'-(Ethane-1,2-diyldisulfonyl)diethanol
Similarity: 0.51
A176859 [104458-24-4]
2-(Methylsulfonyl)ethanamine hydrochloride
Similarity: 0.55
A672347 [7484-34-6]
2,2'-(Ethane-1,2-diyldisulfonyl)diethanol
Similarity: 0.51