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[ CAS No. 20637-09-6 ] {[proInfo.proName]}

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Chemical Structure| 20637-09-6
Chemical Structure| 20637-09-6
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Product Details of [ 20637-09-6 ]

CAS No. :20637-09-6 MDL No. :MFCD07366753
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CLKHQWJXESOLCJ-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :88628
Synonyms :

Calculated chemistry of [ 20637-09-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.33
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.879 mg/ml ; 0.00455 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.293 mg/ml ; 0.00152 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.09 mg/ml ; 0.000466 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 20637-09-6 ]

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

Application In Synthesis of [ 20637-09-6 ]

* 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 [ 20637-09-6 ]
  • Downstream synthetic route of [ 20637-09-6 ]

[ 20637-09-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 20637-02-9 ]
  • [ 20637-09-6 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogen In methanol for 3 h; b) Methyl 4-(4-aminophenyl)butanoateA suspension of methyl 4-(4-nitrophenyl)butanoate (3.05 g, 13.67 mmol) and Pd/C (1.0 g, 10percent Pd on activated C, 1.09 mmol) in MeOH (40 ml_) was stirred under H2 atmosphere (balloon) for 3 h. The reaction mixture was filtered through Celite (washing with EtOAc). Solvent was concentrated off, to furnish 2.33 g of methyl 4-(4-aminophenyl)butanoate (brown solid, yield: 88percent). It was submitted to next step without purification.1H NMR (CDCI3, 250 MHz) δ ppm: 6.96 (d, J = 8.5 Hz, 2H), 6.63 (d, J = 8.2 Hz, 2H), 3.66 (s, 3H), 2.55 (t, J = 7.6 Hz, 2H), 2.31 (t, J = 7.7 Hz, 2H), 1.90 (q, J = 7.6 Hz, 2H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6463 - 6480
[2] Patent: WO2009/80722, 2009, A2, . Location in patent: Page/Page column 52
[3] Journal of Pharmaceutical Sciences, 1988, vol. 77, # 2, p. 185 - 187
[4] Journal of the Chemical Society, 1953, p. 2386,2387
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3014 - 3019
[6] Journal of Pharmaceutical Sciences, 1980, vol. 69, # 1, p. 80 - 84
  • 2
  • [ 67-56-1 ]
  • [ 15118-60-2 ]
  • [ 20637-09-6 ]
YieldReaction ConditionsOperation in experiment
96% for 1.5 h; Reflux A 250-mL round bottom flask was charged with 4-(4-aminophenyl)butyric acid (2.00 g, 11.2 mmol) in methanol (50 mL) and treated with cone, sulfuric acid (1 mL). The resultant mixture was heated to reflux for 1.5 h. After this time, methanol (-25 mL) was distilled off. The reaction was cooled to 60 °C and methyl tert-butyl ether was added. The mixture was allowed to slowly cool to room temperature, then diluted with hexanes (50 mL) to afford a white solid. The solid was dissolved in THF (6 mL)/water (4 mL) and treated with cone. NH4OH (6 mL). The mixture was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with saturated sodium chloride (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (2.07 g, 96percent) as a brown solid. MW = 193.24. ]H NMR (DMSO-i, 500 MHz) δ 6.83-6.79 (m, 2H), 6.50-6.46 (m, 2H), 4.81 (s, 2H), 3.57 (s, 3H), 2.39 (t, J = 7.5 Hz, 2H), 2.25 (t, 7 = 7.5 Hz, 2H), 1.73 (quin, / = 7.5 Hz, 2H).
70% With thionyl chloride In methanol at 0 - 80℃; for 16 h; Synthesis of cyanoamine 28Preparation of methyl 4-(4-aminophenyl)butanoate 27.[00200] To a mixture of compound 26 (0.92 g, 5.13 mmol) in CH30H (20 mL) was added dropwise thionyl chloride (1.9 mL , 25.7 mmol) at OoC with stirring. After addition, the reaction mixture was stirred at 80 oC for 16 h, concentrated in vacuo. The residue was diluted with aqNaHC03, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and concentrated to dryness to give compound 27 (0.7 g, 70percent) as a light yellow solid. 1H NMR (400 MHz, CDC13) 56.97 (d, 2H, J=8.3 Hz), 6.64 (d, 2H, J=8.3 Hz), 3.68 (br s, 2H), 3.66(s, 3H), 2.54 (t, 2H, J=7.4 Hz), 2.3 l(t, 2H, J=7.4 Hz), 1.85- 1.95(m, 2H).
Reference: [1] Patent: WO2014/66659, 2014, A1, . Location in patent: Paragraph 0722
[2] Patent: WO2012/119559, 2012, A1, . Location in patent: Page/Page column 85
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1784 - 1789
[4] Bioorganic and medicinal chemistry letters, 2001, vol. 11, # 21, p. 2847 - 2850
  • 3
  • [ 15118-60-2 ]
  • [ 20637-09-6 ]
YieldReaction ConditionsOperation in experiment
91% With HCl conc.; sodium carbonate In methanol Step 1:
Methyl-4-(4-aminophenyl)-butanoate (40)
To a solution of 4-(4-aminophenyl)-butyric acid (5 g, 27.90 mmol) in MeOH (100 mL) at room temperature was added HCl conc. (37percent 15 mL).
The resulting mixture was stirred overnight at 50° C. then treated with a saturated aqueous solution NaHCO3 and Na2CO3 solid until pH 9.
The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2.
The crude material was purified by flash chromatography using CH2Cl2/MeOH as solvent mixture yielding 40 (4.93 g, 91percent) as orange solid.
1H NMR: (300 MHz, acetone-d6): 6.89 (d, J=8 Hz, 2H), 6.59 (d, J=8 Hz, 2H), 4.40 (broad s, 1H), 3.60 (s, 3H), 2.48 (t, J=7 Hz, 2H), 2.28 (t, J=7 Hz, 2H), 1.82 (qt, J=7 Hz, 2H).
Reference: [1] Patent: US6541661, 2003, B1,
  • 4
  • [ 15118-60-2 ]
  • [ 20637-09-6 ]
YieldReaction ConditionsOperation in experiment
82% With sulfuric acid; sodium carbonate In methanol 9A Methyl 4-(4-aminophenyl)butanoate
8.4 ml of concentrated H2SO4 was added to a solution of 4-(4-aminophenyl)butanoic acid (2.0 g, 11.6 mmo) in methanol (84 ml) and refluxed for 2 h.
After that the mixture was left to cool at room temperature, added with Na2CO3 to basic pH and extracted with ethyl acetate.
The organic phase was dried and the solvent was evaporated off, to obtain 1.7 g of the title compound as a colourless oil (82percent yield).
1H N.M.R. (300 MHz, CD3OD) δ ppm: 1.83 (q, 2H); 2.28 (t, 2H); 2.49 (t, 2H); 3.62 (s, 3H); 6.66 (d, 2H); 6.92 (d, 2H).
Reference: [1] Patent: EP775133, 2001, B1,
  • 5
  • [ 67-56-1 ]
  • [ 67857-97-0 ]
  • [ 5600-62-4 ]
  • [ 20637-09-6 ]
  • [ 46320-17-6 ]
Reference: [1] Patent: EP2388247, 2011, A2, . Location in patent: Page/Page column 8
  • 6
  • [ 15118-60-2 ]
  • [ 18107-18-1 ]
  • [ 20637-09-6 ]
YieldReaction ConditionsOperation in experiment
28% at 0 - 20℃; for 1 h; To a solution of 4-(4-aminophenyl)butanoic acid (180 mg, 1 mmol) in a mixture of THF (4 ml), MeOH (1 ml) and dichloromethane (1 ml) in a 20-mL vial was added dropwise (trimethylsilyl)diazo-methane (1ml, 2N in hexane) at 0 °C. After the addition was complete, the resulting mixture was stirred at room temperature for lhr. The volatile material was removed under reduced pressure and the residue was purified by chromatography on silica gel using hexane/dichloromethane (2:1) followed by dichloromethane as eluent to give methyl 4-(4-aminophenyl)butanoate as an yellowish oil (55 mg, 28percent yield).
Reference: [1] Patent: WO2014/66659, 2014, A1, . Location in patent: Paragraph 0548
  • 7
  • [ 5600-62-4 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1988, vol. 77, # 2, p. 185 - 187
[2] Journal of the Chemical Society, 1953, p. 2386,2387
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6463 - 6480
  • 8
  • [ 198544-23-9 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 84, # 2, p. 119 - 126
  • 9
  • [ 52240-85-4 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 84, # 2, p. 119 - 126
  • 10
  • [ 5473-15-4 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 84, # 2, p. 119 - 126
  • 11
  • [ 103-84-4 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 84, # 2, p. 119 - 126
  • 12
  • [ 198544-22-8 ]
  • [ 20637-09-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 84, # 2, p. 119 - 126
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