Structure of 18671-97-1
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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.
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CAS No. : | 18671-97-1 |
Formula : | C8H4Cl2N2 |
M.W : | 199.04 |
SMILES Code : | ClC1=CC=C2N=C(Cl)C=NC2=C1 |
MDL No. : | MFCD00839695 |
InChI Key : | WFOKVKYNVKVWFK-UHFFFAOYSA-N |
Pubchem ID : | 87748 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.56 |
TPSA ? Topological Polar Surface Area: Calculated from |
25.78 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.1 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.86 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.94 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.21 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.49 |
Solubility | 0.064 mg/ml ; 0.000322 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.06 |
Solubility | 0.173 mg/ml ; 0.00087 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.57 |
Solubility | 0.00542 mg/ml ; 0.0000272 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
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 |
-5.48 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) |
1.72 |
* 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 |
---|---|---|
97% | N, N-dimethylformamide (DMF) (40 mL) was added to a 100 mL reaction flask, and (R) -2- (4-hydroxyphenoxy) Acid (3.0 g, 0.02 mol) was added to the reaction flask and stirred to dissolve. At room temperature, potassium carbonate (4.46 g, 0.033 mol), stirring was continued for 15 to 30 minutes, the temperature was raised to 75 C, and the mixture was stirred for 2 hours. 2,6-dichloroquinoxaline (3.28 g, 0.02 mol) and the temperature was raised to 145 C for 6 h. After completion of the reaction, the mixture was cooled to room temperature, and the reaction solution was poured into ice water (250 mL) and dropped Hydrochloric acid to pH = 4 to 5, filtered, washed with water and dried to give a yellow solid (R) -2- (4 - ((6-chloroquinoxalin-2-yl) oxy) Phenoxy) propionic acid, 5.55 g, The yield was 97%. | |
97% | N, N-dimethylformamide (DMF) (40 mL) was added to a 100 mL reaction flask,(R) -2- (4-hydroxyphenoxy) propionic acid (3.00 g, 0.02 mol) was added to the reaction flask,Stirring dissolved.in room temperature,Potassium carbonate (4.46 g, 0.03 mol) was slowly added in portions,Continue stirring for 15 ~ 30min,Heated to 75 C stirring 2h,Was slowly added 2,6-dichloroquinoxaline (3.28 g, 0.02 mol)The temperature was raised to 145 C for 6 h.After the reaction,Cooled to room temperature,The reaction solution was poured into ice water (250 mL)Dropping dilute hydrochloric acid to pH = 4 to 5,Filter, washed,Dried to give 5.55 g of a yellow solid (R) -2- (4 - ((6-chloroquinoxalin-2-yl) oxy) phenoxy) propionic acid in 97% yield. | |
97% | Was added to a 100 mL reaction flaskN, N-dimethylformamide (DMF) (40 mL)(R) -2- (4-hydroxyphenoxy) propionic acid (3.00 g, 0.02 mol) was added to the reaction flask,Stirring dissolved.Potassium carbonate (4.46 g, 0.033 mol) was slowly added portionwise at room temperature,Continue stirring for 15 ~ 30min, heating to 75 stirring 2h,2,6-dichloroquinoxaline (3.28 g, 0.02 mol) was added slowly,The temperature was raised to 145 C for 6 h. After completion of the reaction, the mixture was cooled to room temperature,The reaction solution was poured into ice water (150 mL), diluted hydrochloric acid was added dropwise to pH = 4 to 5, filtered, washed with water and dried to give a yellow solid(R) -2- (4 - ((6-chloroquinoxalin-2-yl) oxy) phenoxy) propionic acid in a yield of 97%. |
97% | N, N-dimethylformamide (DMF) (40 mL) was added to a 100 mL reaction flask,(R) -2- (4-hydroxyphenoxy) propionic acid (3.00 g, 0.02 mol) was added to the reaction flask,Stirring dissolved. Potassium carbonate (4.46 g, 0.033 mol) was slowly added portionwise at room temperature,Continue stirring for 15 ~ 30min, heating to 75 stirring 2h,Was slowly added 2,6-dichloroquinoxaline (3.28 g, 0.02 mol)The temperature was raised to 145 C for 6 h. After the reaction,Cooled to room temperature,The reaction solution was poured into ice water (250 mL)Dropping dilute hydrochloric acid to pH = 4 to 5,Washed,Dried to give a yellow solid (R) -2- (4 - ((6-chloroquinoxalin-2-yl) oxy)Phenoxy) propionic acid in a yield of 97%. | |
97% | N, N-dimethylformamide (DMF) (40 mL) was added to a 100 mL reaction flask,(R) -2- (4-hydroxyphenoxy) propionic acid (3.0 g, 0.02 mol) was added to the reaction flask,Stirring dissolved.in room temperature,Potassium carbonate (4.46 g, 0.03 mol) was slowly added in portions,Continue stirring for 15 ~ 30min,Heated to 75 C stirring 2h,2,6-dichloroquinoxaline (3.28 g, 0.0165 mol) was slowly added,The temperature was raised to 145 C for 6 h.After the reaction,Cooled to room temperature,The reaction solution was poured into ice water (150 mL)Dropping dilute hydrochloric acid to pH = 4 ~ 5, filtration, washing,Dried to give a yellow solid (R) -2- (4 - ((6-chloroquinoxalin-2-yl) oxy) phenoxy) propionic acid5.55g,The yield was 97%. | |
6.6 g | under room temperature the Potassium carbonate (5.52g,0.04mmol) was added portion wise into the (R)-2-(4-hydroxyphenoxy) propionate (3.64g,0.02mol) of N, N-dimethylformamide solution (40mL) and after strirrng for 15-30 min the temperature was raised to 65-85 C with stirring for 1-2hr. then dropwise added 2,6-dichloro-quinoxaline (3.98g, 0.02mol) and continue to heatup the reaction up to 125~145 C 4~6hr. after Cooled to room temperature, it was poured into ice water (250mL), washed with dilute hydrochloric acid pEta =4~5. The reaction was filtered then washed with water and dried to give the title was a gray solid 6.60g. | |
6.6 g | (R) -2- (4- (6-chloroquinoxalin-2-yloxy) phenoxy)Propionic acid equipped with a magnetic stirrer,Thermometer and condenser 100mL three-necked flask was added N, N-dimethylformamide (DMF) (40mL)And (R) -2- (4-hydroxyphenoxy) propionic acid(0.02 mol),Potassium carbonate (0.04 mol) was added portionwiseAfter stirring at 70-80 C for 0.5 to 1.0 hr,2,6-Dichloroquinoxaline (0.02 mol),After stirring at 130 ~ 140 for 5 ~ 6hr.The reaction was cooled to room temperature,Poured into ice water (250 mL)To the mixture was slowly added dilute hydrochloric acid,Adjusted to pH = 4 ~ 5,filter,Washed,Dried to give the title compound 6.60g |