Structure of 5655-01-6
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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. : | 5655-01-6 |
Formula : | C6H5N3O |
M.W : | 135.12 |
SMILES Code : | N1C2=C(C(N=C1)=O)[NH]C=C2 |
MDL No. : | MFCD09037890 |
InChI Key : | UWMXUDUWVFWJPX-UHFFFAOYSA-N |
Pubchem ID : | 135488881 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 36.71 |
TPSA ? Topological Polar Surface Area: Calculated from |
61.54 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.6 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.37 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.24 |
Solubility | 7.84 mg/ml ; 0.058 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.67 |
Solubility | 29.1 mg/ml ; 0.215 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.41 |
Solubility | 0.522 mg/ml ; 0.00386 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 |
-7.24 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) |
1.73 |
* 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% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 18.0h; | Intermediate 97 (1.70 g, 12.6 mmol) and NBS (2.69 g, 15.1 mmol) were dissolved in DMF (100 mL) and stirred for 18 h. The reaction mixture was diluted with water (50 mL) and the resulting solid was collected by filtration, dried, suspended in MeOH and filtered. The filtrate was concentrated in vacuo to give the title compound as a beige solid (2.60 g,97%). LCMS (ES+): 213.9, 215.9 (M+H)+. |
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18.0h; | Example 49: l-(4-Chloro-5H-pyrrolo[3,2-rf]pyrimidin-7-yl)-2,2,2-trifluoro-l-[l-(4- fluorophenyl)-lH-indazol-5-yl]ethanol; A mixture of 3,5-dihydropyrrolo[3,2-T|pyrimidin-4-one (200 mg, 1.5 mmol, 1 equiv.) and N- bromosuccinimide (320 mg, 1.8 mmol, 1.2 equiv.) in 10 mL of DMF was stirred for 18 hours at room temperature. The reaction was diluted with water and resulting solid was collected by filtration, dried, suspended in MeOH, and filtered. The filtrate was concentrated in vacuo to provide 7-bromo-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a beige solid which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18.0h; | Intermediate 97 (1.70 g, 12.6 mmol) and NBS (2.69 g, 15.1 mmol) were dissolved in DMF (100 mL) and stirred for 18 h. The reaction mixture was diluted with water (50 mL) and the resulting solid was collected by filtration, dried, suspended in MeOH and filtered. The filtrate was concentrated in vacuo to give the title compound as a beige solid (2.60 g, 97%). LCMS (ES+): 213.9, 215.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.3% | In ethanol; at 190℃; | 154 g of 2-amino-3-carboxypyrroleethyl ester was added to 500 ml of ethanol to obtain an organic mixed solution of 2-amino-3-carboxypyrroleethyl ester; and an organic mixed solution of 2-amino-3-carboxypyrroleethyl ester 81 g, i.e., 1 mol of 1,3,5-triazine was added, and the mixture was heated to reflux at 190 C, stirred until the reaction was completed, poured into ice water, filtered, and solid was collected, and solid was then beaten with acetone to obtain 127.3 g of 4-hydroxypyrrolopyrimidine. The yield was 94.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.2% | With formamidine acetic acid; at 120℃; | 150 g of 2-amino-3-carboxypyrroleethyl ester was added to 500 ml of formamide (purchased from Sinopharm Group, density 1.133) to obtain an organic mixed solution of 2-amino-3-carboxypyrroleethyl ester;Add to the organic mixed solution of 2-amino-3-carboxypyrroleethyl ester103gofFormamidine acetate,After raising the temperature to 120 C, and then the temperature was lowered to room temperature, the reaction liquid was poured into ice water, and a solid was collected, and the solid was beaten with acetone to obtain 125 g of 4-hydroxypyrrolopyrimidine (i.e., a compound of the formula V) in a yield of 95.2%. |
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