Structure of 55150-17-9
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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. : | 55150-17-9 |
Formula : | C6H9N3O |
M.W : | 139.16 |
SMILES Code : | NC1=CN=CN=C1OCC |
MDL No. : | MFCD18821948 |
Boiling Point : | No data available |
InChI Key : | XFTNFHPBIWZMBN-UHFFFAOYSA-N |
Pubchem ID : | 45080306 |
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 | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
61.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.54 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.46 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.43 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.13 |
Solubility | 10.2 mg/ml ; 0.0734 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.03 |
Solubility | 13.0 mg/ml ; 0.0933 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.8 |
Solubility | 2.22 mg/ml ; 0.0159 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 |
-7.01 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) |
1.76 |
* 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 |
---|---|---|
94.3% | With sodium hydroxide; hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; at 20.0℃; for 24.0h; | Example 144; N-(4-Ethoxypyrimidin-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (4) 4-Ethoxypyrimidine-5-amine; A mixture of 5-amino-4,6-dichloropyrimidine (5.00 g, 30.5 mmol), tetrahydrofuran (100 ml), sodium hydroxide (2.44 g, 61.0 mmol), ethanol (100 ml) and 10% palladium-carbon (500 mg) was stirred under a hydrogen atmosphere at room temperature for 1 day, insolubles were filtered off and an organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain the desired product (4.00 g, 94.3%) as an oil. 1H-NMR (CDCl3) delta; 1.43 (3H, t, J = 6.9 Hz), 3.75 (2H, br s), 4.48 (2H, q, J = 6.9 Hz), 7.92 (1H, s), 8.24 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With pyridine; In tetrahydrofuran; for 0.5h; | (2) 2,2,2-Trichloroethyl (4-ethoxyprimidin-5-yl)carbamate; To a solution of <strong>[55150-17-9]4-ethoxypyrimidine-5-amine</strong> (1.00 g, 7.19 mmol) and pyridine (1.74 ml, 21.6 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.49 ml, 10.8 mmol) with ice-cooling, the mixture was stirred for 30 minutes with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (1.73 g, 76.5%) as a solid. 1H-NMR (CDCl3) delta; 1.48 (3H, t, J = 7.2 Hz), 4.55 (2H, q, J = 7.2 Hz), 4.87 (2H, s), 7.15(1H, br s), 8.51 (1H, s), 9.20 (1H, br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20 mg | With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h; | To a solution of 2-phenylimidazo[l,2-Z>]pyridazine-8-carboxylic acid (40 mg, 0.167 mmol) and 4-ethoxypyrimidin-5 -amine (46.5 mg, 0.334 mmol) in DMF (2 mL) was added N,N-diisopropylethylamine (0.175 mL, 1.003 mmol) and HATU (127 mg, 0.334 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCCb solution (15 mL). The aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with brine (20 mL), dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography on silica gel (80%? 90% ethyl acetate in hexanes; 24 g column) to afford N-(4-ethoxypyrimidin-5-yl)-2- phenylimidazo[l,2-)]pyridazine-8-carboxarnide (20 mg, 0.055 mmol, 33% yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 12.28 (s, IH), 9.64 (s, IH), 9.17 (s, IH), 8.81 (d, J=4.8 Hz, IH), 8.65 (s, IH), 8.27 - 8.23 (m, 2H), 7.92 (d, J=4.8 Hz, IH), 7.60 - 7.55 (m, 2H), 7.50 - 7.45 (m, IH), 4.79 (q, J=7.0 Hz, 2H), 1.47 (t, J=7.0 Hz, 3H); LCMS (ESI) m/e 361.1 [(M+H) + , calcd for CioHnNeC 361.1]; HPLC (Method A): fe. = 13.50 min; (Method B) = 12.55 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With palladium 10% on activated carbon; hydrogen; sodium hydroxide; In tetrahydrofuran; at 20.0℃; for 24.0h; | A mixture of 2,4-dichloropyrimidin-5 -amine (400 mg, 2.439 mmol), ethanol (12.200 g, 265 mmol), NaOH (195 mg, 4.88 mmol) and 10% palladium on carbon (260 mg, 0.122 mmol) in THF (4 mL) was stirred under a hydrogen atmosphere at room temperature for 24 h. The mixture was concentrated and the residue was purified by column chromatography on silica gel (40%? 70% ethyl acetate in hexanes; 25 g column) to afford 4-ethoxypyrimidin-5 -amine (140 mg, 1.006 mmol, 41% yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 8.03 (s, 1H), 7.85 (s, 1H), 5.07 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 1.35 (t, J=7.0 Hz, 3H); LCMS (ESI) mle 140.1 [(M+H) + , calcd for CeHioNsO 140.1]. |
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