Structure of 882517-92-2
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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. : | 882517-92-2 |
Formula : | C9H5BrN4O |
M.W : | 265.07 |
SMILES Code : | BrC1=CC=C2NC(=O)N3N=CN=C3C2=C1 |
MDL No. : | MFCD14584721 |
InChI Key : | HLXDEXWXUULCPP-UHFFFAOYSA-N |
Pubchem ID : | 135766855 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 13 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 58.81 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.33 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.22 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.2 |
Solubility | 0.169 mg/ml ; 0.000637 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.64 |
Solubility | 0.608 mg/ml ; 0.00229 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.78 |
Solubility | 0.0442 mg/ml ; 0.000167 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) |
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 |
-6.71 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) |
1.88 |
* 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 |
---|---|---|
81% | To a solution of 4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160 C. under a gentle nitrogen sweep. It was cooled to below 100 C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25 C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81%) as a light yellow solid. MS: m/e=264.9/267.0 (M+H+). | |
81% | b) 9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one To a solution of (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160 C. under a gentle nitrogen sweep. It was cooled to below 100 C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25 C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81%) as a light yellow solid. MS: m/e 264.9/267.0 [M+H+]. | |
81% | In 1-methyl-pyrrolidin-2-one; at 160℃; for 1.5h; | To a solution of 4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160 C. under a gentle nitrogen sweep. It was cooled to below 100 C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25 C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81%) as a light yellow solid. MS: m/e=264.9/267.0 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | To a well stirred slurry of <strong>[882517-92-2]9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one</strong> (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100 C., was added aq NaOH 32% (22.4 mL, 241 mmol). The slurry was heated at 140 C. for 17.5 h. The resulting solution was cooled to 27 C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 (M+H+). | |
87% | c) 4-Bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine To a well stirred slurry of <strong>[882517-92-2]9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one</strong> (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100 C., was added aqeous NaOH (32%, 22.4 mL, 241 mmol). The slurry was heated at 140 C. for 17.5 h. The resulting solution was cooled to 27 C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 [M+H+]. | |
87% | c) 4-Bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine To a well stirred slurry of <strong>[882517-92-2]9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one</strong> (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100 C., was added aqueous NaOH (32%, 22.4 ml, 241 mmol). The slurry was heated at 140 C. for 17.5 h. The resulting solution was cooled to 27 C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 [M+H+]. |
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