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[ CAS No. 23687-25-4 ] {[proInfo.proName]}

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Chemical Structure| 23687-25-4
Chemical Structure| 23687-25-4
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Product Details of [ 23687-25-4 ]

CAS No. :23687-25-4 MDL No. :MFCD00034752
Formula : C9H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :ISIUXVGHQFJYHM-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :90237
Synonyms :
4-Aminoisoquinoline

Calculated chemistry of [ 23687-25-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.15
TPSA : 38.91 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.721 mg/ml ; 0.005 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.08 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0693 mg/ml ; 0.000481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 23687-25-4 ]

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

Application In Synthesis of [ 23687-25-4 ]

* 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 [ 23687-25-4 ]
  • Downstream synthetic route of [ 23687-25-4 ]

[ 23687-25-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1532-97-4 ]
  • [ 23687-25-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 1, p. 137 - 149
[2] Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10028 - 10029
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[4] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
[5] Organic Letters, 2014, vol. 16, # 2, p. 556 - 559
[6] Journal of the American Chemical Society, 1942, vol. 64, p. 783
[7] Patent: US2005/20623, 2005, A1, . Location in patent: Page 104
[8] Patent: WO2013/13816, 2013, A1,
[9] Patent: US2013/29995, 2013, A1,
[10] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 4, p. 803 - 806
  • 2
  • [ 1421429-90-4 ]
  • [ 23687-25-4 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride; water In tetrahydrofuran; ethanol at 0 - 23℃; for 3 h; N-(Diphenylmethylene)isoquinolin-4-amine (650 mg, 2.14 mmol) was dissolved in 25 mL tetrahydrofuran and 25 mL ethanol and cooled to 0 °C by using an ice bath. 2M HCl (4.5 mL) was added dropwise at 0° C. The reaction mixture was stirred for another 3 h at room temperature. The reaction mixture was basified by using Na2CO3 to pH≥ 7. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the crude which was purified by column chromatography to isoquinolin-4-amine (296 mg, 97 percent).
97% With hydrogenchloride; water In tetrahydrofuran; ethanol at 0 - 20℃; N-(Diphenylmethylene)isoquinolin-4-amine (650 mg, 2.14 mmol) was dissolved in 25 mL tetrahydrofuran and 25 mL ethanol and cooled to 0° C. by using an ice bath. 2M HCl (4.5 mL) was added dropwise at 0° C. The reaction mixture was stirred for another 3 h at room temperature. The reaction mixture was basified by using Na2CO3 to pH 7. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the crude which was purified by column chromatography to isoquinolin-4-amine (296 mg, 97percent).
Reference: [1] Patent: WO2013/13816, 2013, A1, . Location in patent: Page/Page column 79
[2] Patent: US2013/29995, 2013, A1, . Location in patent: Paragraph 0403-0404
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 4, p. 803 - 806
  • 3
  • [ 1532-97-4 ]
  • [ 23687-25-4 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium amide In 1,2-dimethoxyethane at 80℃; for 20 h; Sealed vial
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333 h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water
4-Bromo-/5O-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdCl2 (7.30 mg, 1.00 x 10"2 mmol), and LiNH2 (0.230 g, 10.0 mmol) in 20.0 mL DME gave 0.118 g (82percent) of 4-Amino-/.yoe-quinoline as a solid.
80%
Stage #1: With ammonia; sodium t-butanolate In 1,2-dimethoxyethane at 90℃; for 20 h;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333 h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water
4-Bromo-λyoe-quinoline (0.208 g, 1.00 mmol), (CyPF-J-Bu)PdCl2 (7.30 mg, 1.00 x 10"2 mmol), and NaOtBu (0.192 g, 2.00 mmol) in 20.0 mL DME gave 0.115 g (80percent) of 4-amino-/-"?-quinoline as a solid Ethyl acetate/methanol: 50/50). 1H NMR (CDCl3) δ 8.70 (s, 1 H), 8.00 (s, 1 H), 7.84 (d, J= 8.0 Hz, 1 H), 7.76 (d,. J = 8.5 Hz, 1 H), 7.58 (dd, J = 8.0, 7.0 Hz, 1 H), 7.51 (dd, J= 8.0, 7.5 Hz, 1 H), 4.21 (s, 2 H); 13C NMR (CDCl3) δ 142.99, 136.86, 128.86, 128.54, 127.99, 127.65, 126.93, 125.95, 119.97.
Reference: [1] Patent: WO2007/109365, 2007, A2, . Location in patent: Page/Page column 48-49; 52
[2] Patent: WO2007/109365, 2007, A2, . Location in patent: Page/Page column 44; 45; 47
  • 4
  • [ 36073-93-5 ]
  • [ 23687-25-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104
[2] Heterocycles, 2004, vol. 63, # 2, p. 283 - 296
  • 5
  • [ 881668-81-1 ]
  • [ 23687-25-4 ]
YieldReaction ConditionsOperation in experiment
53% With sulfuric acid In acetic acid at 100℃; for 6 h; A mixture of N-benzyl-4-aminoisoquinoline (1.00 g5 4.27 mmol), acetic acid (30 mL) and H2SU4 (cone, 7.5 mJL) was stirred at 100 °C for 6 hours. After cooling to rt the reaction was quenched with sat. aq. Na2CO3 (200 mL) and extracted with EtOAc (5χ25 mL). The combined organic phases were concentrated and the residue was purified by chromatography (EtOAc) to give the title compound (325 mg, 53 percent) as a yellow solid.1H NMR (DMSO-J6, 400 MHz) δ 8.49 (s, IH), 8.10 (d, IH), 7.90 (d, IH)3 7.87 (s, IH)5 7.64-7.54 (m, 2H), 5.82 (s, 2H).
Reference: [1] Patent: WO2006/32851, 2006, A1, . Location in patent: Page/Page column 49
  • 6
  • [ 1532-91-8 ]
  • [ 23687-25-4 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 23, p. 5934 - 5937
  • 7
  • [ 1532-97-4 ]
  • [ 23687-25-4 ]
  • [ 194032-33-2 ]
Reference: [1] Patent: EP1074545, 2001, A1,
  • 8
  • [ 20377-03-1 ]
  • [ 23687-25-4 ]
  • [ 92071-67-5 ]
  • [ 92071-68-6 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 7, p. 1501 - 1504
  • 9
  • [ 20377-03-1 ]
  • [ 75-08-1 ]
  • [ 23687-25-4 ]
  • [ 92071-67-5 ]
  • [ 92071-68-6 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 7, p. 1501 - 1504
[2] Heterocycles, 1984, vol. 22, # 7, p. 1501 - 1504
  • 10
  • [ 23687-25-4 ]
  • [ 394-67-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 39, p. 11907 - 11911[2] Angew. Chem., 2016, vol. 128, p. 12086 - 12090,5
[3] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[4] Patent: EP1074545, 2001, A1,
  • 11
  • [ 23687-25-4 ]
  • [ 1532-91-8 ]
Reference: [1] Patent: US2005/20623, 2005, A1, . Location in patent: Page 104
  • 12
  • [ 23687-25-4 ]
  • [ 40073-37-8 ]
Reference: [1] Heterocycles, 2000, vol. 52, # 3, p. 1371 - 1383
  • 13
  • [ 23687-25-4 ]
  • [ 342899-38-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104
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