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[ CAS No. 630125-91-6 ] {[proInfo.proName]}

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Chemical Structure| 630125-91-6
Chemical Structure| 630125-91-6
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Product Details of [ 630125-91-6 ]

CAS No. :630125-91-6 MDL No. :MFCD09909923
Formula : C14H20F3N3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZYWCDXFRHUHFNV-UHFFFAOYSA-N
M.W : 287.32 Pubchem ID :59134564
Synonyms :

Calculated chemistry of [ 630125-91-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 81.16
TPSA : 32.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.72
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.67
Log Po/w (MLOGP) : 2.32
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 2.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.339 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 1.01 mg/ml ; 0.00351 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0363 mg/ml ; 0.000126 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.03

Safety of [ 630125-91-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 630125-91-6 ]

* 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 [ 630125-91-6 ]
  • Downstream synthetic route of [ 630125-91-6 ]

[ 630125-91-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 859027-20-6 ]
  • [ 630125-91-6 ]
YieldReaction ConditionsOperation in experiment
99% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12 h; 1-ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in above was dissolved in methanol, followed by stirring. The reaction solution was added with Pd/C (1.8 g, 17.08 mmol), followed by stirring under hydrogen conditions for about 12 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (19.4 g, 99percent). -NMR Spectrum (300 MHz, DMSO-d6): δ 7.30 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 5.42 (s, 2H), 3.37 (s, 2H), 2.33 (m, 10H) 1.01 (t, 3H) MS(ESI+, m/z): 288 [M+H]+
99% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12 h; 1-ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in <Step 2> above was dissolved in methanol, followed by stirring. The reaction solution was added with Pd/C (1.8 g, 17.08 mmol), followed by stirring under hydrogen conditions for about 12 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (19.4 g, 99percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.30 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 5.42 (s, 2H), 3.37 (s, 2H), 2.33 (m, 10H) 1.01 (t, 3H) MS (ESI+, m/z): 288 [M+H]+
99% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12 h; 1-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in Step (2) above was stirred in a solution of methanol.
The reaction solution was mixed with Pd/C (1.8 g, 17.08 mmol), followed by stirring under hydrogen conditions for about 12 hours at room temperature.
The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol.
The filtrate was concentrated under reduced pressure to obtain the title compound (19.4 g, 99 percent).
1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.30 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 5.42 (s, 2H), 3.37 (s, 2H), 2.33 (m, 10H), 1.01 (t, 3H).
MS (ESI+, m/z): 288 [M+H]+
99% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12 h; 1-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (21.7 g, 68.3 mmol) obtained in Step (2) above was stirred in a solution of methanol.
The reaction solution was mixed with Pd/C (1.8 g, 17.08 mmol), followed by stirring under hydrogen conditions for about 12 hours at room temperature.
The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol.
The filtrate was concentrated under reduced pressure to obtain the title compound (19.4 g, 99percent).
1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.30 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 5.42 (s, 2H), 3.37 (s, 2H), 2.33 (m, 10H), 1.01 (t, 3H).
MS (ESI+, m/z): 288 [M+H]+
71% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 2 h; To the solution of the product of Step B (770 mg, 2.43 mmol) in methanol (10 mL) was added Pd/C (70 mg). The solution was stirred at room temperature under hydrogen (4 atm) for 2 hours. TLC (DCM/MeOH = 20/1) showed the reaction was completed. The resulting solutionwas filtered through a silica pad, the filtrate was concentrated and purified by silica gel chromatography (silica weight: 10 g, eluting: DCMIMeOH = 20/1) to afford the title compound (500 mg, yield: 71percent) as yellow oil. MS: M/e 288(M+1).

Reference: [1] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 37
[2] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0249; 0250; 0251
[3] Patent: EP2876107, 2015, A1, . Location in patent: Paragraph 0090
[4] Patent: US2015/191450, 2015, A1, . Location in patent: Paragraph 0191-0193
[5] Patent: WO2014/206343, 2014, A1, . Location in patent: Page/Page column 81
[6] Patent: WO2009/152356, 2009, A2, . Location in patent: Page/Page column 27
[7] Journal of Medicinal Chemistry, 2010, vol. 53, # 12, p. 4701 - 4719
[8] ChemMedChem, 2016, p. 1587 - 1595
[9] Patent: WO2006/124462, 2006, A2, . Location in patent: Page/Page column 31-32
  • 2
  • [ 1609677-80-6 ]
  • [ 630125-91-6 ]
YieldReaction ConditionsOperation in experiment
69.4% With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 4 h; To a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BH3DMS (19.91 mL, 199 mmol) dropwise. Then the mixture was stirred at 80° C. for 4 h. The mixture was quenched by adding MeOH and then concentrated. The residue was purified by silica column chromatography on silica gel (PE:EA=2:1, Rf=0.35) to give a white solid of 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (14 g, 46.0 mmol, 69.4percent yield): 1H NMR (400 MHz, CDCl3) δ: 7.48 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.8 Hz, 1H), 6.79 (dd, J=2.4, 8.4 Hz, 1H), 3.76 (s, 2H), 3.53 (s, 2H), 2.45-2.39 (m, 8H), 1.08 (t, J=7.2 Hz, 3H); ES-LCMS m/z 288 (M+H).
69.4% With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 4 h; To a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-l-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BH3 DMS (19.91 mL, 199 mmol) dropwise. Then the mixture was stirred at 80 °C for 4 h. The mixture was quenched by adding MeOH and then concentrated. The residue was purified by silica column chromatography on silica gel (PE:EA = 2: 1, Rf = 0.35) to give a white solid of 4-(4-ethyl-piperazin-l-ylmethyl)-3-trifluoromethyl- phenylamine (14 g, 46.0 mmol, 69.4percent yield): lH NMR (400 MHz, CDC13) δ: 7.48 (d, J = 8.4 Hz, 1H), 6.91 (d, J = 2.8 Hz, 1H), 6.79 (dd, J = 2.4, 8.4 Hz, 1H), 3.76 (s, 2H), 3.53 (s, 2H), 2.45-2.39 (m, 8H), 1.08 (t, J= 7.2 Hz, 3H); ES-LCMS m/z 288 (M+H).
69.4% With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 4 h; To a mixture of (4-amino-2-trifluoromethyl-phenyl) - (4-ethyl-piperazin-1-yl) -methanone (20 g 66.4 mmol) in THF (500 mL) was added BH3·DMS (19.91 mL 199 mmol) dropwise. Then the mixture was stirred at 80 for 4 h. The mixture was quenched by adding MeOH and then concentrated. The residue was purified by silica column chromatography on silica gel (PEEA 21 Rf 0.35) to give a white solid of 4- (4-ethyl-piperazin-1-ylmethyl) -3-trifluoromethyl-phenylamine (14 g 46.0 mmol 69.4yield) 1H NMR (400 MHz CDCl3) δ 7.48 (d J 8.4 Hz 1H) 6.91 (d J 2.8 Hz 1H) 6.79 (dd J 2.4 8.4 Hz 1H) 3.76 (s 2H) 3.53 (s 2H) 2.45-2.39 (m 8H) 1.08 (t J 7.2 Hz 3H) ES-LCMS m/z 288 (M+H) .
Reference: [1] Patent: US2014/275111, 2014, A1, . Location in patent: Paragraph 0270; 0273; 0274
[2] Patent: WO2014/141187, 2014, A1, . Location in patent: Page/Page column 52
[3] Patent: WO2016/37578, 2016, A1, . Location in patent: Page/Page column 68
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
  • 3
  • [ 630125-92-7 ]
  • [ 630125-91-6 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
[2] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 102
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
[4] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 102
  • 4
  • [ 694499-22-4 ]
  • [ 630125-91-6 ]
Reference: [1] Patent: WO2013/100632, 2013, A1,
[2] Patent: US2014/371219, 2014, A1,
[3] Patent: WO2014/206343, 2014, A1,
[4] Patent: EP2876107, 2015, A1,
[5] Patent: US2015/191450, 2015, A1,
[6] ChemMedChem, 2016, p. 1587 - 1595
[7] Patent: WO2006/124462, 2006, A2,
  • 5
  • [ 89976-12-5 ]
  • [ 630125-91-6 ]
Reference: [1] Patent: WO2013/100632, 2013, A1,
[2] Patent: US2014/371219, 2014, A1,
[3] Patent: WO2014/206343, 2014, A1,
[4] Patent: EP2876107, 2015, A1,
[5] Patent: US2015/191450, 2015, A1,
[6] ChemMedChem, 2016, p. 1587 - 1595
[7] Patent: WO2006/124462, 2006, A2,
  • 6
  • [ 5308-25-8 ]
  • [ 630125-91-6 ]
Reference: [1] Patent: US2014/275111, 2014, A1,
[2] Patent: WO2014/141187, 2014, A1,
[3] Patent: WO2016/37578, 2016, A1,
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
[5] Patent: WO2006/124462, 2006, A2,
  • 7
  • [ 5308-25-8 ]
  • [ 876322-73-5 ]
  • [ 630125-91-6 ]
  • [ 900254-46-8 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
  • 8
  • [ 393-06-6 ]
  • [ 630125-91-6 ]
Reference: [1] Patent: US2014/275111, 2014, A1,
[2] Patent: WO2014/141187, 2014, A1,
[3] Patent: WO2016/37578, 2016, A1,
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
  • 9
  • [ 630125-84-7 ]
  • [ 630125-91-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
[2] Patent: WO2005/51366, 2005, A2,
  • 10
  • [ 65934-74-9 ]
  • [ 630125-91-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
  • 11
  • [ 350-96-9 ]
  • [ 630125-91-6 ]
Reference: [1] Patent: WO2005/51366, 2005, A2,
  • 12
  • [ 654-70-6 ]
  • [ 630125-91-6 ]
  • [ 900254-46-8 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
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