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[ CAS No. 1005450-55-4 ] {[proInfo.proName]}

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Chemical Structure| 1005450-55-4
Chemical Structure| 1005450-55-4
Structure of 1005450-55-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1005450-55-4 ]

CAS No. :1005450-55-4 MDL No. :MFCD18207041
Formula : C22H20F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :GDEHAOJGPHEOSO-OAHLLOKOSA-N
M.W : 371.40 Pubchem ID :24855929
Synonyms :

Calculated chemistry of [ 1005450-55-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.23
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 100.63
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.45
Log Po/w (XLOGP3) : 5.46
Log Po/w (WLOGP) : 6.5
Log Po/w (MLOGP) : 5.03
Log Po/w (SILICOS-IT) : 6.07
Consensus Log Po/w : 5.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.56
Solubility : 0.00103 mg/ml ; 0.00000276 mol/l
Class : Moderately soluble
Log S (Ali) : -5.83
Solubility : 0.000552 mg/ml ; 0.00000149 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.67
Solubility : 0.0000008 mg/ml ; 0.0000000021 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.57

Safety of [ 1005450-55-4 ]

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 [ 1005450-55-4 ]

* 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 [ 1005450-55-4 ]
  • Downstream synthetic route of [ 1005450-55-4 ]

[ 1005450-55-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1095393-66-0 ]
  • [ 1005450-55-4 ]
YieldReaction ConditionsOperation in experiment
91.2% With hydrogen In methanol; toluene at 20℃; for 1.5 h; hi yet another variation, the reduction of the double bond and amide carbonyl of (E)-N-((i?)-l-naphthalen-l-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-acrylamide is carried out in a stepwise manner. Either the carbonyl group or the alkene double bond can be reduced first. For example, the reduction of the alkene double bond is achieved by hydrogenation in the presence of a metal catalyst.[0123] A suspension of (E)-N-((i?)-l-naphthalen-l-yl-ethyl)-3-(3-trifluoromethyl-phenyl)- acrylamide (1.0 equiv.; 0.67 mmol; 250 mg) and Pd/C 10 wtpercent (25 mg) was stirred in a mixture of methanol and toluene (7 mL/lmL). The reaction flask was evacuated and back filled using a hydrogen filled balloon (three times). The reaction mixture is stirred at room temperature and the progress of the reaction was monitored using high performance liquid chromatography. After 90 minutes, the reaction mixture was filtered over a bed of celite and the solvent from the filtrate was removed in vacuo. The resulting solid was dried overnight at 450C using a vacuum oven. Isolated yield: 91.2percent (229 mg). The identity of the amide was confirmed by 1H NMR and mass spectrometry. (400MHz, CDCl3) δ ppm 1.60 (d, 3H) 2.39- 2.53 (m, 2H) 2.96-3.13 ( m, 2H) 5.55 (br. S., IH) 5.87-5.96 (m, IH) 7.29-7.38 (m, 2H) 7.39- 7.46 (m, 4H) 7.46-7.55 (m, 2H) 7.76-7.82 (m, IH) 7.83-7.89 (m, IH) 8.00-8.07 (m, IH) and HRMS (M+l): 372.1
Reference: [1] Patent: WO2009/2427, 2008, A2, . Location in patent: Page/Page column 39
[2] Patent: WO2008/58235, 2008, A2, . Location in patent: Page/Page column 34
[3] Patent: EP1990333, 2008, A1, . Location in patent: Page/Page column 12
  • 2
  • [ 3886-70-2 ]
  • [ 585-50-2 ]
  • [ 1005450-55-4 ]
YieldReaction ConditionsOperation in experiment
70.87%
Stage #1: With thionyl chloride; N,N-dimethyl-formamide In toluene at 25 - 75℃; for 2 h;
Stage #2: With triethylamine In dichloromethane; toluene at 0 - 5℃; for 1.5 - 2 h;
Example 3: Preparation of N-[I -(R)-(I -naphthyl) ethyl]-3-[3-(trifluoromethyl) phenyl]-l- propanamide(X). Thionyl chloride (6.69 ml, 0.0917 moles) was added dropwise to a solution of 3-[3- (trifluoromethyl) phenyl]-2-propanoic acid (10 gm, 0.045 moles), dimethylformamide (0.5 ml) and dry toluene (100 ml) at 25 - 30 0C under nitrogen atmosphere. The reaction mixture was heated to 70 - 75 0C for 2.0 h. After 2.0 h the toluene was distilled under reduced pressure at 50 - 55 0C. Fresh toluene (100 ml) was further added to reaction mixture to get clear solution. This solution was added dropwise to a solution of ( 1 R)- 1(1- naphthyl)ethane amine (4.88 gm, 0.0285 moles), triethylamine (1 1.53 gm, 0.1 14 moles) in methylene chloride (200 ml) at 0 - 5 0C for 1.5 - 2.0 h under nitrogen atmosphere. After completion of the reaction (by TLC)5 water (50 ml) was added in the reaction mixture and the layers were separated, the organic layer was washed again with water (50 ml). The organic layer was evaporated under reduced pressure to get a crude solid, which was then dissolved in a mixture of hexane (25 ml) and ethyl acetate (30 ml) at reflux and the cooled to O - 5 0C to get solids which was filtered and dried at 50-550C to get the title compound (10 gm, 70.87 percent).Melting point: 108-1110C.IR (KBr) (ν(max), cm-1): 3298.38, 3082.35, 2970.48, 2357.09, 1643.41, 1554.68, 1450.52,1330.93, 1122.61, 1072.48, 798.56, 775.41, 705.97.1H NMR (CDCl3-DMSO-d6) (δ ppm): 7.26 - 8.03 (HH, m), 5.91 (IH, m), 5.58 (IH, bd),3.03 (2H, m), 2.46 (2H, m), 1.60 (3H, d).MS (m/z): 372 [M+l].
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
[2] Patent: WO2008/117299, 2008, A1, . Location in patent: Page/Page column 16-17
[3] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 47 - 52
[4] Patent: WO2008/58235, 2008, A2, . Location in patent: Page/Page column 26
[5] Patent: WO2008/35381, 2008, A2, . Location in patent: Page/Page column 26-27
  • 3
  • [ 1095393-72-8 ]
  • [ 1005450-55-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In methanol at 20℃; for 1 h; Cinacalcet is obtained by reducing the alkyne-amide precursor. In one embodiment, the alkyne was reduced by metal catalyzed hydrogenation. Specifically, to a methanolic solution (7 mL) of 3-(3-trifluoromethyl-phenyl)-propynoic acid ((R)-I- naphthalen-l-yl-ethyl)-amide (1.0 equiv.; 0.68 mmol; 250mg) in a two necked round bottom <n="43"/>flask was added Pd/C 10 wtpercent (28 mg). The flask was evacuated and back filled using a hydrogen filled balloon (three times) before stirring the reaction mixture at room temperature under a positive pressure of hydrogen. Progress of the reaction was monitored by HPLC and LC/MS, with complete reduction of the alkyne group after 1 hour. The reaction was stopped by filtering the reaction mixture over a bed of celite, and the solvent was removed to give a solid that was further dried at 450C overnight in vacuo. Product identity was confirmed by 1H NMR and LC/MS. A quantitative yield of the product was obtained (224mg). (400MHz, CDCl3) δ ppm 1.60 (d, 3H) 2.39-2.53 (m, 2H) 2.96-3.13 ( m, 2H) 5.55 (br. S., IH) 5.87-5.96 (m, IH) 7.29-7.38 (m, 2H) 7.39-7.46 (m, 4H) 7.46-7.55 (m, 2H) 7.76-7.82 (m, IH) 7.83-7.89 (m, IH) 8.00-8.07 (m, IH) and LC/MS (M+l): 372.0.
Reference: [1] Patent: WO2009/2427, 2008, A2, . Location in patent: Page/Page column 41-42
  • 4
  • [ 585-50-2 ]
  • [ 82572-04-1 ]
  • [ 1005450-55-4 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 1, p. 13 - 15
  • 5
  • [ 3886-70-2 ]
  • [ 455-03-8 ]
  • [ 1005450-55-4 ]
Reference: [1] Patent: US2007/259964, 2007, A1, . Location in patent: Page/Page column 3-5
[2] Patent: WO2008/35381, 2008, A2, . Location in patent: Page/Page column 27
[3] Patent: WO2008/35381, 2008, A2, . Location in patent: Page/Page column 27
[4] Patent: CN103739500, 2016, B, . Location in patent: Paragraph 0039; 0047; 0048
  • 6
  • [ 3886-70-2 ]
  • [ 1005450-55-4 ]
Reference: [1] Patent: WO2008/58235, 2008, A2, . Location in patent: Page/Page column 25-28
  • 7
  • [ 3886-70-2 ]
  • [ 294856-02-3 ]
  • [ 1005450-55-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
  • 8
  • [ 1076239-83-2 ]
  • [ 3886-70-2 ]
  • [ 1005450-55-4 ]
Reference: [1] Patent: EP1990333, 2008, A1, . Location in patent: Page/Page column 7-8; 9; 10; 11
  • 9
  • [ 401-78-5 ]
  • [ 1005450-55-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
[2] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
  • 10
  • [ 294856-02-3 ]
  • [ 1005450-55-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
  • 11
  • [ 585-50-2 ]
  • [ 1005450-55-4 ]
Reference: [1] Patent: CN103739500, 2016, B,
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