Structure of 934524-10-4
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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. : | 934524-10-4 |
Formula : | C13H9Cl2N3O2S |
M.W : | 342.20 |
SMILES Code : | O=S(N1C=CC2=C(Cl)N=C(Cl)N=C21)(C3=CC=C(C)C=C3)=O |
MDL No. : | MFCD13193624 |
InChI Key : | DTDGVNQSPAWHTH-UHFFFAOYSA-N |
Pubchem ID : | 53486828 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 21 |
Num. arom. heavy atoms | 15 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 81.58 |
TPSA ? Topological Polar Surface Area: Calculated from |
73.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.13 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.36 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.35 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.96 |
Solubility | 0.00375 mg/ml ; 0.000011 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.37 |
Solubility | 0.00144 mg/ml ; 0.00000422 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.74 |
Solubility | 0.000621 mg/ml ; 0.00000182 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.46 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) |
2.69 |
* 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 N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 90℃; for 3h; | Example 19 N4-(benzo[D]thiazol-5-yl)-N2-(1H-indazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine To a solution of 2,4-dichloro-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.1 g, 0.28 mmol) in n-butyl alcohol (0.8 mL) was added <strong>[1123-93-9]5-aminobenzothiazole</strong> (0.046 g, 0.31 mmol) and DIPEA (0.1 mL, 0.56 mmol) at room temperature. After heating at 90° C. for 3 h, the mixture was diluted with H2O, and the precipitates were collected by filtration to give N-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzolthiazol-5-amine (0.19 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In 1,4-dioxane; at 70℃; for 20h; | A solution of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.584 mmol), <strong>[4138-26-5]nipecotamide</strong> (75 mg, 0.586 mmol) and triethylamine (0.130 mL, 0.934 mmol) in dioxane (5 mL) was stirred at 70 0C for 20 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give l-(2-chloro-7-tosyl- 7H-pyrrolo[2,3-d]pyrimidin-4-yl)<strong>[4138-26-5]piperidine-3-carboxamide</strong> (250 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.2% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; | Add compound 35 (3.4 g, 10 mmol) to a 100 mL single-mouth bottle with magnetic stirringAnd DMF (20 mL), stirred and dissolved, and added compound 36 (1.7 g, 10 mmol)And N,N-diisopropylethylamine (DIPEA, 1.3 g, 10 mmol),The temperature was raised to 110 C under a nitrogen atmosphere and the reaction was stirred overnight. Cool to room temperature,Add water (60 mL), extract with ethyl acetate (50 mL×3),Washed (100 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated.The residue was passed through a silica gel column to give a white solid3.0g,The yield was 63.2%. |
63.2% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; | Compound 10a (3.4 g, 10 mmol) was added to a 100 mL single-mouth bottle with magnetic stirring.And DMF (20 mL), stirred and dissolved, and added compound 11a (1.7 g, 10 mmol)And DIPEA (1.3g, 10mmol),The temperature was raised to 110 C under a nitrogen atmosphere and stirred to react overnight. Cool to room temperature,Add water (60 mL), extract with ethyl acetate (50 mL×3),Washed (100 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated.The residue was passed through a silica gel column to give a white solid3.0 g, the yield was 63.2%. |
With N-ethyl-N,N-diisopropylamine; at 100℃; for 5.0h; | General procedure: To a solution of 8 (1 equiv) in n-BuOH (20mL), corresponding amines (1.1 equiv) and N-ethyl-N-isopropylpropan-2-amine (1.2 equiv) were added. The mixture was stirred at 100C for 5h. The mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over Na2SO4, filtered, and evaporated. The resulting intermediate was purified by chromatography. |
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