Structure of 116008-52-7
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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. : | 116008-52-7 |
Formula : | C4H5N3O2 |
M.W : | 127.10 |
SMILES Code : | O=C(C1=C(N)C=NN1)O |
MDL No. : | MFCD09991897 |
InChI Key : | SHRRRNSPESGSCM-UHFFFAOYSA-N |
Pubchem ID : | 22566198 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 29.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
92.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-0.06 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.37 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.94 |
Solubility | 14.5 mg/ml ; 0.114 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.43 |
Solubility | 4.71 mg/ml ; 0.037 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.21 |
Solubility | 78.6 mg/ml ; 0.618 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 |
-7.11 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 |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
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) |
1.52 |
* 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 pyridine; In N-methyl-acetamide; | EXAMPLE 125 Trans-3-(naphth-2-yl)-but-2-enoic acid-N-(3-carboxy-1H-pyrazol-4-yl)-amide Prepared analogously to Example 31 from trans-3-(naphth-2-yl)-but-2-enoic acid chloride and <strong>[116008-52-7]4-amino-1H-pyrazol-3-carboxylic acid</strong> in dimethylformamide with the addition of pyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Scheme 33--Route to Preferred Groups 49 [4,3-d] ring fusion Nitration of pyrazole-3-carboxylic acid followed by reduction gives 4-aminopyrazole-3-carboxylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate; In water; for 30.0h;Reflux; | General procedure: Reduction of the nitrogroup was carried out according to a published method.21The corresponding nitro acid 1, 3 (0.032 mol) wassuspended in H2O (30 ml). Activated carbon (0.8 g),N2H4·H2O (95%, rho 1.023 g/cm3) (6.55 ml, 6.71 g, 0.134 mol),and FeCl3·6H2O (64 mg) were added to the suspension withstirring. The reaction mixture was heated under reflux for30 h. The hot solution was filtered, the filtrate wasevaporated to dryness under reduced pressure. Theresulting dry residue was dissolved in H2O (20 ml) andcarefully acidified with 2 M aqueous HCl to pH 4-5. Theformed precipitate was filtered off and washed with a smallamount of H2O. The product was dried in a vacuumdesiccator over P2O5 to constant weight. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | General procedure: The corresponding amino acid2, 4 (0.0173 mol) was dissolved in 2 aqueous l (50 ml),and the formed solution was cooled to 0 in an ice bath.Aqueous NaNO2 (0.019 mol) was dropwise added to thereaction mixture. The mixture was stirred for 30 min, thenaqueous NaN3 (0.026 mol) was carefully added. Thereaction mixture was stirred for 3-4 h. The formed precipitatewas filtered off on a fritted glass filter and washed witha small amount of H2O, then dried in a vacuum desiccatorover P2O5 to constant weight. The filtrate was extractedwith EtOAc, the organic phase was separated and driedover anhydrous Na2SO4. The dried organic phase wasevaporated under reduced pressure on the rotary evaporatorto afford a solid. Both solids were combined. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With thionyl chloride; for 12.0h;Reflux; | Amino acid 4 (2 g, 0.0157 mol) wassuspended in absolute EtOH (20 ml). SOCl2 (1.17 ml,1.92 g, 0.0161 mol) was added dropwise to the suspension.The mixture was heated under reflux for 12 h untilhomogenization. A cherry-colored solution formed. Thesolvent was evaporated to dryness under reduced pressureon the rotary evaporator. The solid residue was dried in avacuum desiccator to constant weight. Yield 3.0 g (99%),pink solid, mp 114-115C. 1H NMR spectrum (400 MHz, DMSO-d6), delta, ppm (J, Hz): 10.22 (4, br. s, NH, +NH3);8.03 (1H, s, -3 pyrazole); 4.28 (2, q, J = 7.0,OCH2H3); 1.30 (3, t, J = 7.1, OCH2H3). 13C NMRspectrum (101 MHz, DMSO-d6), delta, ppm: 160.5; 133.7;127.3; 116.6; 60.8; 14.1. Found, m/z: 178.05868 [M+Na]+.C6H9N3NaO2. Calculated, m/z: 178.05870. |
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