Structure of 4490-82-8
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 4490-82-8 |
Formula : | C4H12ClNO |
M.W : | 125.60 |
SMILES Code : | NOCCCC.[H]Cl |
MDL No. : | MFCD00487631 |
InChI Key : | HUYRNQWVAPCTQZ-UHFFFAOYSA-N |
Pubchem ID : | 12283956 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 32.1 |
TPSA ? Topological Polar Surface Area: Calculated from | 35.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.38 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.48 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.04 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.76 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.29 |
Solubility | 6.44 mg/ml ; 0.0513 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.72 |
Solubility | 2.37 mg/ml ; 0.0189 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -0.76 |
Solubility | 21.7 mg/ml ; 0.173 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) | 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 | -6.09 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 | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 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) | 1.64 |
* 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 |
---|---|---|
100% | Stage #1: With methylhydrazine In dichloromethane at 0 - 20℃; for 2 h; Stage #2: With hydrogenchloride In 1,4-dioxane at 0℃; | After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.38 ml of 1-iodinated butane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) and then dried to obtain 635 mg of a compound (yield: 95percent). The compound was dissolved in 5 ml of dichloromethane, and 0.12 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 257 mg of a solid (yield: 100percent). 13 mg of the obtained solid and 44 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1015 (44 mg, yield: 88percent). 1H-NMR (300 MHz, CDCl3) δ5.91-5.76 (m, 2H), 5.34-5.33 (m, 1H), 5.28-5.25 (m, 1H), 5.15 (m, 1H), 4.25-4.10 (m, 3H), 4.02-3.97 (m, 2H), 3.59-3.48 (m, 1H), 2.42-0.60 (m, 42H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.38 ml of 1-iodinated butane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60 C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) and then dried to obtain 635 mg of a compound (yield: 95%). The compound was dissolved in 5 ml of dichloromethane, and 0.12 ml of methyl hydrazine (TCI) was slowly added at 0 C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0 C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 257 mg of a solid (yield: 100%). 13 mg of the obtained solid and 44 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80 C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1015 (44 mg, yield: 88%). 1H-NMR (300 MHz, CDCl3) delta5.91-5.76 (m, 2H), 5.34-5.33 (m, 1H), 5.28-5.25 (m, 1H), 5.15 (m, 1H), 4.25-4.10 (m, 3H), 4.02-3.97 (m, 2H), 3.59-3.48 (m, 1H), 2.42-0.60 (m, 42H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium acetate; In methanol; at 20℃; for 5h; | 500 mg (2.2 mmol) of the compound obtained in Preparation Example 36 (2), 286 mg (2.5 mmol) of 2-fluoroethoxyamine hydrochloride, and 406 mg (4.9 mmol) of sodium acetate were added to 10 ml of methanol, and the resulting solution was reacted for 5 hours at room temperature. After the reaction, solvent was removed and 10 ml of ethylacetate was added thereto, followed by washing twice with 10 ml of water. An organic layer was separated and dried over anhydrous magnesium sulfate, then the residue was purified by column chromatography (ethylacetate/hexane = 3/7) to obtain 628 mg (2.2 mmol) of the title compound in a yield of 99%. NMR : lH-NMR (CDCl3) 6 7. 08-7. 00 (2H, m), 6. 75-6. 72 (2H, m), 4.61 (1H, brs), 4. 60-4. 47 (2H, m), 4. 29-4. 18 (2H, m), 3.67 (3H, s), 3.51 (1H, t, J=8Hz), 3. 19-3. 13 (1H, m), 2. 93-2. 88 (1H, m), 1.89 (3H, s) Mass (EI) 284 (M++1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; | 5.8 g (0.017 mol) of methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloxime and 2.5 g (0.020 mol) of n-<strong>[4490-82-8]butoxyamine hydrochloride</strong> in 60 ml of methanol are stirred at room temperature for 24 hours. The mixture is then hydrolyzed with water and extracted with methyl tert-butyl ether. The organic phase is washed with water, dried and concentrated. 5.0 g (71%) of the title compound are obtained as a colorless oil (compound no. 470). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; di-isopropyl ether; | (a) 2-Furyl-(4-hydroxy-phenyl)ketone-(O-butyl oxime) A solution of 2-furyl-(4-hydroxy-phenyl)ketone (50 g) and <strong>[4490-82-8]butoxyamine hydrochloride</strong> (36 g) in methanol (250 ml) is maintained 6 hours at its refluxing temperature. The solvent is then removed and the residue is dissolved in diisopropyl oxide (400 ml), the organic phase is washed with aqueous acidic and basic solutions and then with water. After drying the solution, the solvent is evaporated off, to give 46 g of oxime (mixture of both stereoisomers) having a melting point of 58 C. Separation of the isomers may be effected by fractional crystallization or by column chromatography through silica, using chloroform as eluent, for example. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Similarly, 1-ethoxy-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea and 1-butoxy-3-(4,5,6,7-tetrahydrobenzo[b]-thien-4-yl)urea are prepared by using ethoxyamine hydrochloride and n-<strong>[4490-82-8]butoxyamine hydrochloride</strong>, respectively, in place of methoxyamine hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In methanol; at 20℃; for 3h;Product distribution / selectivity; | Step 3: Preparation of 2-(3-Bromo-quinolin-6-yloxy)-N-(2-butoxyimino-1 , 1 -dimethyl- ethyl)-2-methylsulfanyl-acetamide 2-(3-Bromo-quinolin-6-yloxy)-N-(1 ,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide (0.1 g) from Stage 2, Step 2 above, pyridine (0.022 ml) and <strong>[4490-82-8]O-n-butyl-hydroxylamine hydrochloride</strong> (0.035 g) in methanol (5 ml) were stirred at rt for 3 hours. The reaction mixture was diluted with ethyl acetate and poured onto sat. NaHCO3 (30 ml). The two phases were separated and the aqueous layer was extracted with ethyl acetate (3x50 ml). The organic layers were combined, dried over magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 3:1) to give 2-(3-bromo-quinolin-6-yloxy)-N-(2-butoxyimino-1 ,1-dimethyl-ethyl)-2- methylsulfanyl-acetamide as white solid (0.115 g). 1H NMR (CDCI3) delta ppm: 8.81 (1 H, d); 8.24 (1 H1 d); 8.04 (1 H1 d); 7.71 (1 H, s); 7.45 (1 H, dd); 7.39 (1 H1 s); 7.17 (1H, d); 5.64 (1 H, s); 4.08 (2H1 1); 2.19 (3H1 s); 1.68-1.58 (8H, m); 1.45-1.36 (2H, m), 0.94 (3H1 1). |
Tags: 4490-82-8 synthesis path| 4490-82-8 SDS| 4490-82-8 COA| 4490-82-8 purity| 4490-82-8 application| 4490-82-8 NMR| 4490-82-8 COA| 4490-82-8 structure
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