Structure of 113583-35-0
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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. : | 113583-35-0 |
Formula : | C7H10N2O4S |
M.W : | 218.23 |
SMILES Code : | C1=C(N=C([S](C)(=O)=O)N=C1OC)OC |
MDL No. : | MFCD00672151 |
InChI Key : | ITDVJJVNAASTRS-UHFFFAOYSA-N |
Pubchem ID : | 838363 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
86.76 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 |
0.38 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.9 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.44 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.55 |
Solubility | 6.13 mg/ml ; 0.0281 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.77 |
Solubility | 3.73 mg/ml ; 0.0171 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.23 |
Solubility | 1.29 mg/ml ; 0.00592 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 |
-7.36 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) |
2.23 |
* 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 |
---|---|---|
82% | 2.8 6 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide,Then 0.3 g (12 mmol) sodium hydride was added.The mixture was stirred for 1 hour,Then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added.After stirring at room temperature for 24 hours,Carefully hydrolyze with 10 ml of water,The pH was adjusted to 5 with acetic acid,The solvent was removed by distillation under high vacuum.The residue was placed in 100 ml of ethyl acetate,Wash with water,And dried over magnesium sulfate,The solvent was distilled off.The residue was mixed with 10 ml of ether,The resulting precipitate was collected by suction filtration.After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C. | |
In N-methyl-acetamide; water; ethyl acetate; | Example 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h, cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C. | |
In N-methyl-acetamide; water; ethyl acetate; | EXAMPLE 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h. and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h., cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; | Step E Synthesis of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde as an intermediate Under a nitrogen atmosphere a solution of 2.0 grams (0.013 mole) of 6-chlorosalicylaldehyde in 10 mL of dimethylformamide was stirred, and 1.94 grams (0.0141 mole) of potassium carbonate was added. The reaction mixture was then stirred for 10 minutes, and a solution of 2.6 grams (0.013 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared in Steps A-C) in 15 mL of dimethylformamide was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was warmed to 60° C. where it was stirred for 18 hours. The reaction mixture was poured into 150 mL of water, cooled, and the pH was adjusted to 12 with aqueous 50percent sodium hydroxide, with stirring. The mixture was stirred for 15 minutes, and the resultant solid was collected by filtration to yield 1.62 grams of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In n-heptane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; | EXAMPLE 6 Preparation of (S)-methyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate (Compound II; R'=ethyl, R=methoxy) To a stirred solution of (S)-methyl-2-hydroxy-3-methoxy-3,3-diphenylpropionate (compound IV;50 gms/0.174 moles) and potassium carbonate (26.36 gms/0.191 moles) in DMF (500 ml) was added 4,6-Dimethoxy-2-(methyl sulfonyl)pyrimidine (compound III; R=methoxy) (41.42 gms/0.191 moles) in a dry flask under nitrogen at 25-30 C. The reaction mass was heated to 90-92 C. and further stirred for 1.5 hour. The reaction mass was charged with ethyl acetate (1.5 lit).The organic layer was washed with 2N citric acid (500 ml) followed by water and treated with charcoal. The clear filtrate was distilled completely under vacuum. The residue was stirred with n-heptane (200 ml), filtered, washed with n-heptane (120 ml) and dried to obtain 56 gms of compound (II). The compound (II) was dissolved in acetonitrile (1.12 lit) and isolated in water (2.8 lit). The solid was isolated by filtration and dried to obtain 49 gms of compound (II). Efficiency: 66.10% Purity by HPLC:99.1% Chiral purity: 99.4% |
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