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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 35303-76-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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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.
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CAS No. : | 35303-76-5 |
Formula : | C8H12N2O2S |
M.W : | 200.26 |
SMILES Code : | O=S(C1=CC=C(CCN)C=C1)(N)=O |
MDL No. : | MFCD00010301 |
InChI Key : | FXNSVEQMUYPYJS-UHFFFAOYSA-N |
Pubchem ID : | 169682 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 |
Class: | 8 |
UN#: | 3259 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 49.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
94.56 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.92 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.12 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.1 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.36 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.12 |
Solubility | 15.3 mg/ml ; 0.0762 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.36 |
Solubility | 8.73 mg/ml ; 0.0436 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.42 |
Solubility | 0.763 mg/ml ; 0.00381 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 |
No |
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 |
-7.64 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 |
0.0 |
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) |
1.62 |
* 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 pyridine; sodium acetate; In water; acetone; benzene; | (a) 4-(beta-N'-2-quinolyl-N'-methylureidoethyl)-benzene-sulfonamide 76.5 Grams of <strong>[52430-43-0]2-methylaminoquinoline</strong> were mixed in 600 ml of absolute benzene with 39.5 g of pyridine and, while cooling with ice and stirring, treated with 49 g of phosgene. Stirring was continued for 1 hour, the salt precipitated was suction-filtered and washed well with benzene. The filtrate was evaporated, the residue taken up in 100 ml of acetone and added dropwise, while stirring and cooling with ice, to a mixture which contained in 290 ml of water 0.36 mol of 4-(beta-aminoethyl)-benzenesulfonamide and 0.72 mol of sodium acetate and was mixed with 290 ml of acetone. Stirring was continued for about 1 hour, the mixture was mixed with water, suction-filtered and recrystallized from ethanol - dimethylformamide. The reaction product obtained melted at 185-187 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere; | General procedure: Reactions of (1R)-(-)-10-camphorsulfonyl chloride 1 and (1S)-(+)-10-camphorsulfonyl chloride 2 (0.3 g,1.0 equiv) with amino derivatives 3 - 7 (1.0 equiv) were carried out at 0 C to room temperature in Schotten-Baumann conditions under nitrogen atmosphere, in the presence of a stoichiometric amount of dropwised dry TEA (1.0 equiv for 3, 5, 6 and 2.0 equiv for 4, 7), in dry DMF as solvent (2 ml). When complete (monitoring by TLC), reactions were quenched with crushed ice, extracted with ethyl acetate (20 ml), washed with 1 N HCl (2 x 10 ml) and brine (2 x 10 ml). The collected organic phase was dried on anhydrous Na2SO4, filtered and evaporated under vacuum. The crude was purified by silica gel column chromatography eluting with n-hexane/ethyl acetate or DCM/methanol to afford compounds 8-17 as white solids in medium yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium acetate; acetic anhydride; acetic acid; for 12h;Reflux; | General procedure: A mixture of 4-(2-aminoethyl)benzenesulfonamide (0.5 g,2.5 mmol), anhydrous sodium acetate (0.41 g, 5.0 mmol) and anacid anhydride (2.5 mmol) was stirred in glacial acetic acid(15 mL). The mixture was heated under reflux for 12 h and thereaction was monitored with the help of TLC. After completion ofreaction the solvent was removed under reduced pressure andthe crude solid obtained was washed with water, dried and recrystallisedfrom an appropriate solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In tetrahydrofuran; at 20℃; | 3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85%); mp 183-185 C.1H NMR (400 MHz, DMSO-d6): delta = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): delta = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140. |
85.5% | In isopropyl alcohol; for 6h;Reflux; | The compound Kappa 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g and isopropanol 50g were heated under reflux for 6 h (4-(2-aminoethyl)benzenesulfonamide remaining 0.79%), cooled to After drying at 25 C, filtration and 50 C, 6.12 g of compound I was obtained. The purity of the solution was 98.66% by HPLC, the impurity was 0.60%, and the impurities V and VI were not detected. The yield was 85.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.6% | With propionic acid; In isopropyl alcohol; for 7.5h;Reflux; | 10.0 g of the compound, 8.16 g of 4-(2-aminoethyl)benzenesulfonamide, 3.02 g of propionic acid and 50 g of isopropanol were heated under reflux for 7.5 h, cooled at 25 C, filtered and dried at 50 C to give the compound 113.52 g. , the yield was 94.4%, the purity of the HPLC method was 99.63%, the impurity was 0.06%, and the impurities V and VI were not detected. |
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