Structure of 17420-30-3
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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. : | 17420-30-3 |
Formula : | C7H5N3O2 |
M.W : | 163.13 |
SMILES Code : | NC1=CC=C(C=C1C#N)N(=O)=O |
MDL No. : | MFCD00007362 |
InChI Key : | MGCGMYPNXAFGFA-UHFFFAOYSA-N |
Pubchem ID : | 28532 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 44.38 |
TPSA ? Topological Polar Surface Area: Calculated from |
95.63 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.67 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.62 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.31 |
Solubility | 0.802 mg/ml ; 0.00492 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.46 |
Solubility | 0.0568 mg/ml ; 0.000348 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.97 |
Solubility | 1.73 mg/ml ; 0.0106 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) |
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 |
-6.0 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 |
2.0 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) |
1.57 |
* 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 sulfuric acid; at 130℃; for 0.666667h; | Step 1 A mixture of 2-amino-5-nitrobenzonitrile (25.4 g) and sulfuric acid (70 mL) was stirred at 130C for 40 min. The reaction mixture was added slowly to ice water, and the precipitate was collected by filtration, washed with water, ethanol and diethyl ether to give 2-amino-5-nitrobenzamide (24.6 g). | |
24.63 g | With sulfuric acid; at 130℃; for 0.666667h; | Step 1 A mixture of 2-amino-5-nitrobenzonitrile (25.39 g) and sulfuric acid (70 ml) was stirred at 130 C. for 40 min. The reaction mixture was gradually added to ice water, and the precipitate was collected by filtration and washed with water, ethanol and diethyl ether to give 2-amino-5-nitrobenzamide (24.63 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With KCC-1/IL NPs; at 70℃; under 6000.6 Torr; for 1h;Autoclave; | General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate. |
91% | With fibrous nanosilica functionalized with sodium tripolyphosphate and 3-aminopropyltriethoxysilane; In neat (no solvent); at 70℃; under 11251.1 Torr; for 0.833333h;Autoclave; Green chemistry; | General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials. |
81% | With {Eu[N(SiMe3)2](mu-O:kappa2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 100℃; for 24h; | Under anhydrous, anaerobic, argon protection, 0.0999 g (7.5 × 10 -5 mol){L2Eu [N (SiMe3) 2] · THF} 2, followed by 11.2 muL (7.5 × 10 -5 mol) of DBU,Under the protection of carbon dioxide bag, add 2mL dimethyl sulfoxide,After adding 0.3107 g (1.5 x 10-3 mol) of 2-amino-5-nitrobenzonitrile,The reaction was stirred in a constant temperature bath at 100 C. After 24 hours,The reaction was quenched by adding 5 mL of 2 mol / L hydrochloric acid and suction filtration. The solid was washed with 3 × 5 mL of hydrochloric acid, then with toluene and ether, the residual solvent was removed and the solid was dried to give the product in a yield of 81% |
1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; under 760.051 Torr; | SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a <n="13"/>benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described, | |
(1) DBU(32.7 g) was added to a solution of 2-amino-5-nitrobenzonitrile(11.69 g) in DMF(135 mL) at room temperature and the mixture was stirred under carbon dioxide atmosphere at room temperature overnight. The reaction solution was cooled to 0C, and 1N hydrochloric acid(1350 mL) was added dropwise. The precipitated crystals were filtered, washed with diethyl ether and dried to give 6-nitro-1H-quinazolin-2,4-dione(14.13 g) as a yellow powder. APCI-MS(m/e):206[M-H]-. |
Tags: 17420-30-3 synthesis path| 17420-30-3 SDS| 17420-30-3 COA| 17420-30-3 purity| 17420-30-3 application| 17420-30-3 NMR| 17420-30-3 COA| 17420-30-3 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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