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[ CAS No. 362052-00-4 ] {[proInfo.proName]}

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Chemical Structure| 362052-00-4
Chemical Structure| 362052-00-4
Structure of 362052-00-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 362052-00-4 ]

CAS No. :362052-00-4 MDL No. :MFCD20547529
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YSVNGBYVEJEXGO-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :22569863
Synonyms :

Calculated chemistry of [ 362052-00-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.51
TPSA : 61.09 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.18
Solubility : 1.17 mg/ml ; 0.00668 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.498 mg/ml ; 0.00284 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.901 mg/ml ; 0.00514 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 362052-00-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P311 UN#:2811
Hazard Statements:H302-H312-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 362052-00-4 ]

* 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.

  • Upstream synthesis route of [ 362052-00-4 ]
  • Downstream synthetic route of [ 362052-00-4 ]

[ 362052-00-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 118618-32-9 ]
  • [ 362052-00-4 ]
YieldReaction ConditionsOperation in experiment
99% With water; sodium hydroxide In tetrahydrofuran at 20℃; Step 0 (Intermediate A): see example 85.[0556]Step 1: To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHCO3. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. ethyl 2-(4-bromophenyl)acetate (2.1 g) was obtained as 91percent yield.[0557]Step 2: To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1.5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1.0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49percent yield.[0558]Step 3: To a stirred solution of ethyl 2-(4-cyanophenyl)acetate (0.8 g, 4.101 mmol) in anhydrous dimethylformamide were added 60percent sodium hydride (180 mg, 4.511 mol) and Iodo methane were added after 10 min with an ice bath. The reaction mixture was stirred for 1 h hours, quenched with water and extracted with ethylacetate which is washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure. The residue was purified by column chromatography. Ethyl 2-(4-cyanophenyl)propanoate (453 mg) was obtained as 48percent[0559]Step 4: To a stirred solution of ethyl 2-(4-cyanophenyl)propanoate (453 mg, 1.968 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (197 mg, 4.919 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3-4 with acetic acid. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyanophenyl)propanoic acid (422 mg) was obtained as 99percent yield.[0560]Step 5: To a stirred solution of 2-(4-cyanophenyl)propanoic acid (148 mg, 0.85 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (243 mg, 1.27 mmol), 1-hydroxybenzotriazole (171 mg, 1.27 mmol), (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (247 mg, 0.93 mmol) and triethylamine (0.29 mL, 2.11 mmol). The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (311 mg) was obtained as 87percent yield.[0561]Step 6: To a stirred solution of 2-(4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (305 mg, 0.72 mmol) in ethanol was cooled to 0° C. and added NiCl2.6H2O (17 mg, 0.072 mmol) and stirred more then 15 min. Sodium borohydride (191 mg, 5.04 mmol) was then added in small portions. The reaction was exothermic and effervescent. The resulting reaction mixture was allowed to warm to room temperature and left to stir for 2 hour. The mixture was filtered using celite pad. The filtrate was concentrated was evaporated. The residue was dissolved in ethylacetate and washed with water and brine, but when it does not separate easily, small amount of 1N HCl and saturated NaHCO3 was used. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg) was obtained as 64percent yield.[0562]Step 7: To a stirred solution of 2-(4-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg, 0.39 mmol) in dichloromethane the intermediate (A) (117 mg, 0.39 mmol) and triethylamine (0.20 mL, 0.56 mmol) was added was stirred for overnight. The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with dichloromethane and washed with water, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was purified by column chromatography. Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg) was obtained as 50percent yield.[0563]Step 8: To a stirred solution of tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg, 0.19 mmol) in dichloromethane (5 mL) cooled by ice bath and trifluoroacetic acid (4.0 mL) was added. The reaction mixture was stirred for overnight. The mixture was diluted with dichloromethane and then washed with NaHCO3, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and purified by column chromatography. 2-(4-((Sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 88) (79 mg) was obtained as 79percent yield.[0564]1H NMR (300 MHz, CDCl3) δ 7.76 (d, 1H, J=7.86 Hz), 7.58 (s, 1H, J=7.86 Hz), 7.27-7.32 (m, 3H), 7.10-7.24 (m, 5H), 5.59 (bs, 1H), 4.69 (bs, 1H), 4.58 (s, 2H), 4.44 (d, 2H, J=6.03 Hz), 4.26 (d, 2H, J=6.21 Hz), 3.50 (m, 1H), 2.38 (s, 3H), 1.46 (d, 3H, J=7.14 Hz).
95%
Stage #1: With sodium hydroxide In tetrahydrofuran; water at 20℃;
Stage #2: With acetic acid In tetrahydrofuran; water
Step 4: To a stirred solution of ethyl 2-(4-cyanophenyl)propanoate (832 mg, 4.09 mmol) in co-solvent with tetrahydrofuran and water (1 :1 ) were added sodium hydroxide (409 mg, 10.23 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3-4 with acetic acid. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyanophenyl)propanoic acid (805 g) was obtained as 95 percent yield.
Reference: [1] Patent: US2013/79377, 2013, A1, . Location in patent: Paragraph 0554; 0559
[2] Patent: WO2013/45451, 2013, A1, . Location in patent: Page/Page column 51
[3] Patent: WO2013/45447, 2013, A1, . Location in patent: Page/Page column 83
[4] Patent: US2013/79320, 2013, A1, . Location in patent: Paragraph 0473; 0477
  • 2
  • [ 125670-62-4 ]
  • [ 362052-00-4 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium hydroxide; water In tetrahydrofuran for 2.25 h;
Stage #2: With water; citric acid In tetrahydrofuran
Step C; The title compound from Step B above (672 mg) was dissolved in THF (10 mL) and a solution of lithium hydroxide monohydrate (300 mg) in water (10 mL) was added. The mixture was vigorously stirred for 21/4 h, acidified with 10percent citric acid and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to afford the title compound (623 mg; quant.) as bright yellow crystals. [MH]+=176.
Reference: [1] Patent: US2008/21024, 2008, A1, . Location in patent: Page/Page column 79
  • 3
  • [ 3435-51-6 ]
  • [ 124-38-9 ]
  • [ 362052-00-4 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3198 - 3201
[2] Chemical Communications, 2017, vol. 53, # 21, p. 3098 - 3101
[3] Journal of the American Chemical Society, 2008, vol. 130, # 45, p. 14936 - 14937
  • 4
  • [ 3435-51-6 ]
  • [ 201230-82-2 ]
  • [ 362052-00-4 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 32, p. 3967 - 3970
  • 5
  • [ 124-38-9 ]
  • [ 1253037-62-5 ]
  • [ 362052-00-4 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 39, p. 7732 - 7737
  • 6
  • [ 124-38-9 ]
  • [ 362052-00-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 16, p. 5053 - 5057[2] Angew. Chem., 2016, vol. 128, # 16, p. 5137 - 5141,5
  • 7
  • [ 3435-51-6 ]
  • [ 124-38-9 ]
  • [ 362052-00-4 ]
  • [ 25309-65-3 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 21, p. 3098 - 3101
[2] Chemical Communications, 2017, vol. 53, # 21, p. 3098 - 3101
  • 8
  • [ 124-38-9 ]
  • [ 20488-11-3 ]
  • [ 362052-00-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 119, p. 98721 - 98723
  • 9
  • [ 124-38-9 ]
  • [ 101219-69-6 ]
  • [ 362052-00-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6772 - 6776
  • 10
  • [ 1878-68-8 ]
  • [ 362052-00-4 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
[2] Patent: US2013/79377, 2013, A1,
[3] Patent: US2013/79320, 2013, A1,
  • 11
  • [ 14062-25-0 ]
  • [ 362052-00-4 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
[2] Patent: US2013/79377, 2013, A1,
[3] Patent: US2013/79320, 2013, A1,
  • 12
  • [ 1528-41-2 ]
  • [ 362052-00-4 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
[2] Patent: US2013/79377, 2013, A1,
[3] Patent: US2013/79320, 2013, A1,
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