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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 942199-59-9
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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
*For Research Use Only !
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CAS No. : | 942199-59-9 |
Formula : | C8H3ClF3NO2S |
M.W : | 269.63 |
SMILES Code : | O=S(C1=CC=C(C#N)C(C(F)(F)F)=C1)(Cl)=O |
MDL No. : | MFCD16041567 |
InChI Key : | YKHLEJBYHQQAMZ-UHFFFAOYSA-N |
Pubchem ID : | 54592428 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.24 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.54 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.92 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.26 |
Solubility | 0.147 mg/ml ; 0.000545 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.59 |
Solubility | 0.0693 mg/ml ; 0.000257 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.91 |
Solubility | 0.033 mg/ml ; 0.000122 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) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
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 |
-6.13 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.21 |
* 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 |
---|---|---|
41% | With pyridine; In dichloromethane; at 0 - 20℃; for 17.0h; | Step 3: (S)-N-(l-(3-(4-cyano-3-(trifluoromethyl)phenylsulfonamido)phenyl)- 2-(pyrrolidin-l -yl)ethyl)-2-(3,4-dichlorophenyl)-N-methylacetamide, hydrochloride salt. [0075] N-[(15 -l-(3-Aminophenyl)-2-(pyrrolidin-l-yl)ethyl]-2-(3,4-dichlorophenyl)- N-methylacetamide (2) (0.12 g, 0.30 mmol) was dissolved in dichloromethane (6 mL) and anhydrous pyridine (0.18 mL, 2.27 mmol). To the cooled (0 C) yellow solution there was added dropwise 4-cyano-3-(trifluoromethyl)benzene-l-sulfonyl chloride (0.21 g, 0.75 mmol) in dichloromethane (1 mL). The yellow reaction mixture was stirred at 0 C, and the color turned orange. The reaction mixture was allowed to equilibrate to room temperature. After approximately 17 hours at room temperature, the reaction mixture was diluted with dichloromethane (25 mL) and followed by the addition of water (30 mL). The aqueous portion was extracted with dichloromethane (2 x 15 mL). In five separate washing steps, the combined organic portions were washed in the following sequence: a IN hydrochloric acid wash, a water wash, a saturated sodium bicarbonate wash, a second water wash and a brine wash (35 mL each). The organic portion was dried over anhydrous sodium sulfate, filtered, concentrated and purified by chromatography to give 0.08 g (41%) (S)-N-(l-(3-(4-cyano-3- (trifluoromethyl)phenylsulfonamido)phenyl)-2-(pyrrolidin-l-yl)ethyl)-2-(3,4- dichlorophenyl)-N-methylacetamide as a yellow oil. XH NMR (500 MHz, CDC13): delta 6.89 - 8.09 (m, 10H), 5.89 (m, 1H), 3.59 - 3.75 (m, 2H), 3.12 (m, 1H), 2.68 (m, 4H), 2.50 (m, 2H), 1.14 (m, 3H); MS (EI) for C29H27CI2F3N4O3S: 639(MH+). [0076] The compound was converted into the hydrochloride salt by dissolving the oil in acetonitrile and adding IN hydrochloric acid. The solution was lyopholized to give the hydrochloride salt as an off-white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; copper(l) iodide; thionyl chloride; sodium nitrite; In water; acetone; at 0 - 20℃; for 1.0h; | Anhydrous cuprous chloride (0.3 g, 0.003 mol, 0.011 eq.) Was added to 500 ml of water, and 80 ml of dichlorosulfoxide was added dropwise under an ice-water bath, and rt overnight to obtain solution a;4-amino-2- (trifluoromethyl) benzonitrile (50.0 g, 0.269 mol, 1.0 eq.)Add 260ml of concentrated hydrochloric acid and 50ml of acetone in an ice water bath.Add sodium nitrite (20.4g, 0.296mol,1.1eq.) Dissolved in 20ml of water, stirred at 0 C for 30min,Get reaction solution a;Then add the reaction solution a dropwise to the solution a, and react at room temperature for 30 minutes.TLC monitors for complete response. |
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