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[ CAS No. 167301-82-8 ] {[proInfo.proName]}

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Chemical Structure| 167301-82-8
Chemical Structure| 167301-82-8
Structure of 167301-82-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 167301-82-8 ]

CAS No. :167301-82-8 MDL No. :MFCD22375314
Formula : C6H14ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UJBLPIIKAPQKLR-UHFFFAOYSA-N
M.W : 167.63 Pubchem ID :21466688
Synonyms :

Calculated chemistry of [ 167301-82-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.72
TPSA : 44.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.35
Log Po/w (WLOGP) : 0.9
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 0.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.03
Solubility : 15.5 mg/ml ; 0.0925 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 23.8 mg/ml ; 0.142 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.73
Solubility : 31.0 mg/ml ; 0.185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.94

Safety of [ 167301-82-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 167301-82-8 ]

* 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.

  • Downstream synthetic route of [ 167301-82-8 ]

[ 167301-82-8 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 616-30-8 ]
  • [ 167301-82-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; toluene-4-sulfonic acid In water; 2,2-dimethoxy-propane 1.A A) A) 2,2-Dimethyl-5-aminomethyl-1,3-dioxolane hydrochloride (ICJ-115) 182.2g (2 moles) of 3-amino-1,2-propandiol are dissolved in 540 ml of water. Then 35% hydrochloric acid is added until pH 1 - 2 is reached, and the mixture is stirred at the ambient temperature for 15 minutes. The solvent is then evaporated upto dryness. A suspension of the resultant residue is made in 1.2 l of 2,2 - dimethoxypropane. 15.0 g of p-toluenesulphonic acid are added and the mixture is vigorously stirred under reflux for half an hour. The precipitated solid is filtered, washed with acetone and dried in a vacuum. 313 g are obtained (93%)
  • 2
  • [ 1445-45-0 ]
  • [ 167301-82-8 ]
  • [ 1690784-66-7 ]
YieldReaction ConditionsOperation in experiment
96% In methanol at 135℃; for 0.25h; Microwave irradiation; General procedure for the preparation of acetamides 3a-3u (via microwave irradiation) General procedure: To a solution of 1.5 eq trimethyl orthoacetate in 2 mL MeOH was added amine hydrochloride (0.0015 mol). After heating via microwave irradiation to 135°C for 15 minutes, the product was isolated by concentration in vacuo to give essentially pure acetamides. In general, these reactions were accompanied by an expected but slight increase in pressure - none exceeded the pressure limits of the instrument.
  • 3
  • [ 22195-47-7 ]
  • [ 167301-82-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine hydrochloride In ethanol for 2h; Reflux; General procedure for the preparation of amine hydrochloride salts 2c-2r General procedure: To a 25-mL round-bottomed flask containing ammonium chloride (0.54 g, 10 mmol) was added ethanol (3 mL) followed by the requisite amine (10 mmol). The mixture was magnetically stirred and refluxed for 2 h. The solvent was then removed by rotary evaporation affording the hydrochloride salt as a solid invariably in quantitative yield.
  • 4
  • [ 167301-82-8 ]
  • [ 52788-50-8 ]
  • [ 1613470-64-6 ]
YieldReaction ConditionsOperation in experiment
10.9 g With triethylamine In acetonitrile for 1h; Reflux; 2.2 (2) Preparation of 2-[(2,2-dimethyl-[1,3] dioxolan-4-ylmethyl)amino] -N-dodecylacetamide General procedure: C-(2,2-Dimethyl[1,3]dioxolan-4-yl)methylamine hydrochloride (4.2 g) (see EP 647618) was dissolved in acetonitrile (100 mL) and triethylamine (7 mL) was added. 2-bromo-N-dodecyl-acetamide (5.35 g) obtained in (1) was added to this solution, followed by warm reflux for 1 hour. After cooling to room temperature, all acetonitrile was distilled off under reduced pressure, and extracted with water (100 mL) and dichloromethane (100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and then separated by column chromatography (ethyl acetate: methanol = 30: 1) to give 2.77 g of a pale yellow liquid.
  • 5
  • [ 167301-82-8 ]
  • [ 15537-87-8 ]
  • [ 1613470-62-4 ]
YieldReaction ConditionsOperation in experiment
2.77 g With triethylamine In acetonitrile for 1h; Reflux; 1.2 (2) Preparation of 2-[(2,2-dimethyl-[1,3] dioxolan-4-ylmethyl)amino] -N-dodecylacetamide C-(2,2-Dimethyl[1,3]dioxolan-4-yl)methylamine hydrochloride (4.2 g) (see EP 647618) was dissolved in acetonitrile (100 mL) and triethylamine (7 mL) was added. 2-bromo-N-dodecyl-acetamide (5.35 g) obtained in (1) was added to this solution, followed by warm reflux for 1 hour. After cooling to room temperature, all acetonitrile was distilled off under reduced pressure, and extracted with water (100 mL) and dichloromethane (100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and then separated by column chromatography (ethyl acetate: methanol = 30: 1) to give 2.77 g of a pale yellow liquid.
  • 6
  • [ 167301-82-8 ]
  • [ 2590867-43-7 ]
  • [ 2590867-44-8 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 5-((4-methoxybenzyl)(5-(4-(trifluoromethyl)phenyl)oxazol-2-yl)amino)picolinonitrile With sodium In methanol Reflux; Stage #2: rac-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine hydrochloride In methanol for 16h; Reflux; 1.91 Sodium metal (0.044 g, 1.9 mmol) was dissolved in anhydrous MeOH (2 mL) and then added to a suspension of 5-((4-methoxybenzyl)(5-(4-(trifluoromethyl)phenyl)oxazol-2- yl)amino)picolinonitrile (0.172 g, 0.38 mmol) in anhydrous MeOH (2 mL). The reaction mixture was stirred at rt for 0.5 h then refluxed for a further 1 h. rac-(2,2-Dimethyl-1,3- dioxolan-4-yl)methanamineHCl (0.255 g, 1.52 mmol) was added to the mixture. The reaction mixture was refluxed for 16 h to provide rac-N-((2,2-dimethyl-1,3-dioxolan-4- yl)methyl)-5-((4-methoxybenzyl)(5-(4-(trifluoromethyl)phenyl)oxazol-2- yl)amino)picolinimidamide in yield 84% (0.186 g).1H NMR (401 MHz, MeOH-d4) d 9.03 (s, 1H), 8.24 (d, J = 7.3 Hz, 1H), 8.16 (d, J = 8.2 Hz, 1H), 7.78 (d, J = 8.0 Hz, 2H), 7.72 (d, J = 7.8 Hz, 2H), 7.60 (s, 1H), 7.32 (d, J = 8.0, 2H), 6.91 (d, J = 8.2 Hz, 2H), 5.41 (s, 2H), 4.50 (m, 1H), 4.19 (m, 1H), 3.87-3.72 (m, 6H), 1.43 (s, 3H), 1.37 (s, 3H). LCMS Rf (min) = 3.642, MS m/z = 582.3 [M + H]+
  • 7
  • [ 616-30-8 ]
  • [ 77-76-9 ]
  • [ 167301-82-8 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 3-Amino-1,2-propanediol With hydrogenchloride In water at 20℃; for 0.333333h; Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid for 1h; Reflux;
  • 8
  • [ 167301-82-8 ]
  • [ 2604488-91-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane 1.2: 24 h / 0 - 25 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 50 °C
  • 9
  • [ 167301-82-8 ]
  • [ 124-63-0 ]
  • [ 170215-77-7 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: rac-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine hydrochloride With triethylamine In dichloromethane Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 25℃; for 24h;
  • 10
  • [ 167301-82-8 ]
  • [ CAS Unavailable ]
  • [ 2566623-72-9 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide In toluene at 100℃; for 2h; Inert atmosphere; 48.4 Step 4 Compound 48c (0.1 g, 214.46 µmol) was added to toluene (2 mL), and then sodium tert-butoxide (61.83 mg, 643.39 µmol), (2,2-dimethyl-1,3-dioxolane-4-yl)methylamine hydrochloride (26.71 mg, 42.89 µmol) and tris(dibenzylideneacetone)dipalladium (19.64 mg, 21.45 µmol) were added thereto. The air was replaced with nitrogen three times, and the reaction solution was stirred at 100 °C for 2 hours. The reaction solution was concentrated to dryness under reduced pressure. The crude was purified by preparative high performance liquid chromatography (chromatographic column: Waters Xbridge BEH C18 100 30 mm 10 µm; mobile phase: [water (10 mM ammonium bicarbonate)-acetonitrile]; B (acetonitrile)%: 35%-60%, 8 min) to obtain compound 48.LCMS (ESI) m/z: 517.4[M+1]+1H NMR (400 MHz, DMSO-d6) δ 9.00 - 9.08 (m, 1H), 8.61 - 8.67 (m, 1H), 8.25 - 8.34 (m, 2H), 8.00 - 8.10 (m, 2H), 7.90 - 7.98 (m, 1H), 7.55 - 7.64 (m, 1H), 7.29 - 7.36 (m, 1H), 7.00 - 7.09 (m, 2H), 5.99 - 6.07 (m, 1H), 4.25 - 4.35 (m, 1H), 4.04 - 4.13 (m, 1H), 3.85 - 3.93 (m, 3H), 3.68 - 3.78 (m, 1H), 3.23 - 3.29 (m, 2H), 1.35 - 1.41 (m, 3H), 1.27 - 1.33 (m, 3H).
With tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide In toluene at 100℃; for 2h; Inert atmosphere; 48.4 Step 4 Compound 48c (0.1 g, 214.46 µmol) was added to toluene (2 mL), and then sodium tert-butoxide (61.83 mg, 643.39 µmol), (2,2-dimethyl-1,3-dioxolane-4-yl)methylamine hydrochloride (26.71 mg, 42.89 µmol) and tris(dibenzylideneacetone)dipalladium (19.64 mg, 21.45 µmol) were added thereto. The air was replaced with nitrogen three times, and the reaction solution was stirred at 100 °C for 2 hours. The reaction solution was concentrated to dryness under reduced pressure. The crude was purified by preparative high performance liquid chromatography (chromatographic column: Waters Xbridge BEH C18 100 30 mm 10 µm; mobile phase: [water (10 mM ammonium bicarbonate)-acetonitrile]; B (acetonitrile)%: 35%-60%, 8 min) to obtain compound 48.LCMS (ESI) m/z: 517.4[M+1]+1H NMR (400 MHz, DMSO-d6) δ 9.00 - 9.08 (m, 1H), 8.61 - 8.67 (m, 1H), 8.25 - 8.34 (m, 2H), 8.00 - 8.10 (m, 2H), 7.90 - 7.98 (m, 1H), 7.55 - 7.64 (m, 1H), 7.29 - 7.36 (m, 1H), 7.00 - 7.09 (m, 2H), 5.99 - 6.07 (m, 1H), 4.25 - 4.35 (m, 1H), 4.04 - 4.13 (m, 1H), 3.85 - 3.93 (m, 3H), 3.68 - 3.78 (m, 1H), 3.23 - 3.29 (m, 2H), 1.35 - 1.41 (m, 3H), 1.27 - 1.33 (m, 3H).
  • 11
  • [ 167301-82-8 ]
  • [ 2566624-33-5 ]
  • [ 2566623-77-4 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide In toluene at 100℃; for 2h; Inert atmosphere; 52.2 Step 2 (2,2-dimethyl-1,3-dioxolane-4-yl)methylamine hydrochloride (216.17 mg, 1.29 mmol, 214.03 µL, HCl) and compound 52a (0.5 g, 1.07 mmol) were added to toluene (10 mL), and then sodium tert-butoxide (309.81 mg, 3.22 mmol), tris(dibenzylideneacetone) dipalladium (133.82 mg, 214.92 µmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (98.40 mg, 107.46 µmol) were added thereto. The air was replaced with nitrogen three times, and the reaction solution was stirred at 100 °C for 2 hours. To the reaction solution were added ethyl acetate (200 mL) and water (100 mL) for extraction and phase separation. The organic phase was dried, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (dichloromethane:methanol = 100 : 1 to 10 : 1) to obtain a crude. The crude was purified by preparative high performance liquid chromatography (chromatographic column: Waters Xbridge Prep OBD C18 150 40 mm 10 µm; mobile phase: [water (10 mM ammonium bicarbonate)-acetonitrile]; B (acetonitrile)%: 45%-70%, 8 min) to obtain compound 52 LCMS (ESI) m/z: 516.2[M+1]+1H NMR (400 MHz, DMSO-d6) δ 8.99 - 9.06 (m, 1H), 8.25 - 8.34 (m, 2H), 8.01 - 8.05 (m, 1H), 7.92 - 7.99 (m, 1H), 7.53 - 7.69 (m, 2H), 7.31 - 7.40 (m, 1H), 7.15 - 7.23 (m, 1H), 6.91 - 7.04 (m, 2H), 6.62 - 6.70 (m, 1H), 5.90 - 6.01 (m, 1H), 4.24 - 4.34 (m, 1H), 4.03 - 4.13 (m, 1H), 3.81 - 3.97 (m, 3H), 3.66 - 3.75 (m, 1H), 3.21 - 3.28 (m, 2H), 1.15 - 1.51 (m, 6H).
With tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide In toluene at 100℃; for 2h; Inert atmosphere; 52.2 Step 2 (2,2-dimethyl-1,3-dioxolane-4-yl)methylamine hydrochloride (216.17 mg, 1.29 mmol, 214.03 µL, HCl) and compound 52a (0.5 g, 1.07 mmol) were added to toluene (10 mL), and then sodium tert-butoxide (309.81 mg, 3.22 mmol), tris(dibenzylideneacetone) dipalladium (133.82 mg, 214.92 µmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (98.40 mg, 107.46 µmol) were added thereto. The air was replaced with nitrogen three times, and the reaction solution was stirred at 100 °C for 2 hours. To the reaction solution were added ethyl acetate (200 mL) and water (100 mL) for extraction and phase separation. The organic phase was dried, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (dichloromethane:methanol = 100 : 1 to 10 : 1) to obtain a crude. The crude was purified by preparative high performance liquid chromatography (chromatographic column: Waters Xbridge Prep OBD C18 150 40 mm 10 µm; mobile phase: [water (10 mM ammonium bicarbonate)-acetonitrile]; B (acetonitrile)%: 45%-70%, 8 min) to obtain compound 52 LCMS (ESI) m/z: 516.2[M+1]+1H NMR (400 MHz, DMSO-d6) δ 8.99 - 9.06 (m, 1H), 8.25 - 8.34 (m, 2H), 8.01 - 8.05 (m, 1H), 7.92 - 7.99 (m, 1H), 7.53 - 7.69 (m, 2H), 7.31 - 7.40 (m, 1H), 7.15 - 7.23 (m, 1H), 6.91 - 7.04 (m, 2H), 6.62 - 6.70 (m, 1H), 5.90 - 6.01 (m, 1H), 4.24 - 4.34 (m, 1H), 4.03 - 4.13 (m, 1H), 3.81 - 3.97 (m, 3H), 3.66 - 3.75 (m, 1H), 3.21 - 3.28 (m, 2H), 1.15 - 1.51 (m, 6H).
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