Structure of 51940-64-8
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CAS No. : | 51940-64-8 |
Formula : | C7H6Cl2N2O2 |
M.W : | 221.04 |
SMILES Code : | C1=C(C(=NC(=N1)Cl)Cl)C(=O)OCC |
MDL No. : | MFCD09910281 |
InChI Key : | SRJBDGLSCPDXBL-UHFFFAOYSA-N |
Pubchem ID : | 104020 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.08 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.96 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.35 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.98 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.83 |
Solubility | 0.328 mg/ml ; 0.00149 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.07 |
Solubility | 0.187 mg/ml ; 0.000845 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.37 |
Solubility | 0.0936 mg/ml ; 0.000424 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 |
-5.99 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.89 |
* 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 |
---|---|---|
99% | In tetrahydrofuran; at 20℃; for 0.166667h; | 11.2: 2,4-Dichloropyrimidine-5-carboxylic acid ethyl ester Compound 11.1 (13.5 g, 64 mmol) is dissolved in THF (100 ml). Ethanol (15 ml) is added and the mixture is stirred at ambient temperature for 10 min. The solvents are evaporated and an oil is recovered and hydrolyzed with a saturated K2CO3 solution and extracted with AcOEt (3*250 ml). The organic phase is washed with an NaCl solution (100 ml) and dried over Na2SO4. After filtering and evaporating, an orange oil is recovered (14 g, yd: 99%). 1H NMR, d6-DMSO (300 MHz): 9.16 (s, 1H), 4.37 (q, 2H, J=7.11 Hz), 1.34 (t, 3H, J=7.11 Hz). |
99% | In tetrahydrofuran; at 20℃; for 0.166667h;Inert atmosphere; | 9.2: 2,4-Dichloropyrimidine-5-carboxylic Acid Ethyl Ester; In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 13.5 g (64.0 mmol) of above compound are dissolved in 100 ml of anhydrous THF. 15 ml of absolute ethanol are added and the mixture is stirred for 10 min at ambient temperature. The mixture is diluted with a saturated aqueous solution of K2CO3 (100 ml) and extracted with ethyl acetate (4×100 ml). The organic phases are combined and then washed with 150 ml of a saturated aqueous solution of NaCl. After separation, the organic phase is dried over MgSO4 and filtered, and the solvent is evaporated off under reduced pressure, so as to obtain 14.0 g (63.3 mmol) of compound in the form of an orange oil. Yield=99%. 1H NMR DMSO d6 (300 MHz): 1.34 (t, J=7.1 Hz, 3H); 4.37 (q, J=7.1 Hz, 2H); 9.16 (s, 1H). |
With N-ethyl-N,N-diisopropylamine; at 0℃; for 0.5h;Inert atmosphere; | A solution of <strong>[2972-52-3]2,4-dichloropyrimidine-5-carbonyl chloride</strong> (1.00 g, 4.76 mmol) in ethanol (6.0 mL) was added DIPEA (2.5 raL, 14,4 mmol) slowly at 0 C under nitrogen. After 30 mm, hex-5-yn-1-amine (0.476 g, 4.91 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 3.5 h, then was added dropwise to a solution of 6-azidohexan-1-amine (0.801 g, 5.64 mmol) in ethanol (4.0 mL) at 50 C After the reaction was complete (monitored by LCMS), the mixture was diluted with water (10 mL) and concentrated under a reduced pressure and filtered. The yellow solid was washed with water and dried under vacuum to be used in the next step without further purification (0.723 g, 39% over 3 steps). |
With N-ethyl-N,N-diisopropylamine; at 0℃; for 0.5h;Inert atmosphere; | Ethyl 2,8,9J0J7J9.22-heptaazatricvclori6.3.1. .l0ltricosa-l(2U (23 8 8(22I19- entaene-21 -carboxylate (1279) (1280) A solution of 2,4-dicMoropyrirnidine-5-carbonyl chloride (1.00 g, 4.76 mmol) in ethanol (6.0 mL) was added DIPEA (2.5 mL, 14.4 mmol) slowly at 0 C under nitrogen. After 30 min, hex-5-yn-l -amine (0.476 g, 4.91 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 3.5 h, then was added drop wise to a solution of 6-azidohexan-l -amine (0.801 g, 5.64 mmol) in ethanol (4.0 mL) at 50 C. After the reaction was complete (monitored by LCMS), the mixture was diluted with water (10 mL) and concentrated under a reduced pressure and filtered. The yellow solid was washed with water and dried under vacuum to be used in the next step without further purification (0.723 g, 39% over 3 steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate; In acetonitrile; at 17 - 25℃; for 16h;Inert atmosphere; | Potassium carbonate (62.5 g, 452 mmol) was added to ethyl 2,4-dichloropyrimidine-5- carboxylate (40 g, 181 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (24.9 g, 181 mmol) in acetonitrile (1000 mL). The reaction mixture was stirred at rt for 16 h. The precipitate was collected by filtration, washed with THF (750 mL) and the organic layers were removed under reduced pressure. The crude product was purified by fee, elution gradient 0 to 2percent THF in DCM, to afford the title compound (37.7 g, 73percent) as a pale yellow solid; 1H NMR (400 MHz, DMSO) 1.32 (3H, t), 1.54 - 1.63 (2H, m), 1.85 - 1.89 (2H, m), 3.46 (2H, td), 3.85 (2H, dt), 4.19 (1H, dtt), 4.31 (2H, q), 8.34 (1H, d), 8.64 (1H, s); mJz MH+286. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium carbonate; In acetonitrile; at 17 - 25℃; for 16h;Inert atmosphere; | Potassium carbonate (78 g, 565 mmol) was added to ethyl 2,4-dichloropyrimidine-5- carboxylate (50.0 g, 226 mmol) and <strong>[56239-26-0]cis-4-aminocyclohexanol hydrochloride</strong> (34.3 g, 226 mmol) in acetonitrile (700 mL) at rt under air. The reaction mixture was stirred at rt for 16 h. The mixture was filtered through a Celite pad. The filtrate was concentrated under reduced pressure. The precipitate was collected by filtration, washed with MeCN (100 mL) and dried under vacuum to afford the title compound (41.0 g, 61percent) as a white solid; 1H NMR (400 MHz, DMSO) 1.32 (3H, t), 1.42 - 1.58 (2H, m), 1.60 - 1.75 (6H, m), 3.66 (1H, d), 4.06 (1H, dd), 4.33 (2H, q), 4.57 (1H, d), 8.46 (1H, d), 8.63 (1H, s); m/z MH+ 300. |
Tags: 51940-64-8 synthesis path| 51940-64-8 SDS| 51940-64-8 COA| 51940-64-8 purity| 51940-64-8 application| 51940-64-8 NMR| 51940-64-8 COA| 51940-64-8 structure
A109465 [3177-20-6]
Methyl 2,4-dichloropyrimidine-5-carboxylate
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A340483 [41103-17-7]
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A163747 [36745-93-4]
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A404089 [1240597-30-1]
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A173615 [89793-12-4]
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A109465 [3177-20-6]
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A340483 [41103-17-7]
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