Structure of 54709-94-3
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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. : | 54709-94-3 |
Formula : | C5H6N2O |
M.W : | 110.11 |
SMILES Code : | CC1=CC(NN=C1)=O |
MDL No. : | MFCD09743644 |
InChI Key : | MMDFKVYPOQFQHP-UHFFFAOYSA-N |
Pubchem ID : | 327041 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 29.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.75 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.05 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.55 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.5 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.86 |
Solubility | 15.1 mg/ml ; 0.137 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.16 |
Solubility | 76.3 mg/ml ; 0.693 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.88 |
Solubility | 1.44 mg/ml ; 0.0131 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 |
-7.21 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) |
1.66 |
* 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 |
---|---|---|
87% | With potassium permanganate; sulfuric acid; at 45℃; for 1.0h; | Example 386-Oxo-1,6-dihydro-pyridazine-4-carboxylic acid The title compound from Example 37 (0.90 g, 8.2 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45 C. Potassium permanganate (3.6 g, 12 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45 C. The reaction was then cooled to room temperature and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.98 g (87%) of the title compound as the a pale green solid.1H NMR (300 MHz, CDCl3): delta (ppm) 13.39 (broad s, 1H), 8.12 (s, 1H), 7.22 (s, 1H). |
87% | With potassium permanganate; sulfuric acid; at 45℃; for 1.0h; | 6-Oxo-l,6-dihydro-pyridazine-4-carboxylic acidThe title compound from Example 18.2 (0.90 g, 8.17 mmol) was stirred in concentrated sulfuric acid (13 mL) and heated to 45 0C. Potassium permanganate (3.6 g, 12.25 mmol) was added portion wise over 30 min to avoid letting the temperature rise. The reaction was allowed to stir for a further 30 min at 45 0C. The reaction was then cooled to r.t. and ice was added to the reaction mixture. The resulting precipitate was collected by vacuum filtration, washing with cold water and diethyl ether to give 0.978 g (87%) of the title compound as the a pale green solid. 1H NMR (300 MHz, CDCl3) delta 13.39 (br, IH), 8.12 (s, IH), 7.22 (s, IH). |
77% | Example 306-Oxo-1,6-dihydro-pyridazine-4-carboxylic acid To a stirred solution of the title compound of Example 29 (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60 C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the title compound (4.5 g, 77%).1H NMR (400 MHz, (CD3)2SO): delta (ppm) 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H). |
77% | With dipyridinium dichromate; sulfuric acid; at 50 - 60℃; for 0.5h; | Step 14B: 6-Oxo-1H-pyridazine-4-carboxylic acid; To a stirred solution of the subtitle compound of Step 14A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60 C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the subtitle compound (4.5 g, 77%).1H NMR (400 MHz, (CD3)2SO): delta 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H). |
77% | With potassium dichromate; sulfuric acid; at 50 - 60℃; for 0.5h; | Step 10B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid; To a stirred solution of the subtitle compound of Step 10A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for 10 min at 60 C., the viscous green mixture was poured on crushed ice. The solids were filtered off and washed with cold water. After drying in vacuo the subtitle compound was isolated (4.5 g, 77%).1H NMR (400 MHz, DMSO-d6): delta 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H). |
77% | With potassium dichromate; sulfuric acid; at 50 - 60℃; for 0.5h; | Step 7B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic Acid To a stirred solution of the subtitle compound of Step 7A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60 C., then the viscous green mixture was poured on crushed ice. The solid powder, which separated, was collected, washed with cold water and dried to give the subtitle compound (4.5 g, 77%).1H NMR (400 MHz, (CD3)2SO): delta 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H). |
77% | With potassium dichromate; sulfuric acid; at 60℃; for 0.166667h; | Step 13B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid To a stirred solution of the subtitle compound of Step 13A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60 C., the viscous green mixture was poured on crushed ice. The solids were filtered off and washed with cold water. After drying in vacuo the subtitle compound was isolated (4.5 g, 77%). 1H NMR (400 MHz, (CD3)2SO): delta 7.22 (s, 3H), 8.13 (s,1H), 13.38 (s, broad, 1H). |