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[ CAS No. 23687-26-5 ] {[proInfo.proName]}

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Chemical Structure| 23687-26-5
Chemical Structure| 23687-26-5
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Product Details of [ 23687-26-5 ]

CAS No. :23687-26-5 MDL No. :MFCD04114862
Formula : C9H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NGFCTYXFMDWFRQ-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :588991
Synonyms :

Calculated chemistry of [ 23687-26-5 ]

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) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.58 mg/ml ; 0.00402 mol/l
Class : Soluble
Log S (Ali) : -2.0
Solubility : 1.45 mg/ml ; 0.0101 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 : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 23687-26-5 ]

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 [ 23687-26-5 ]

* 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 [ 23687-26-5 ]
  • Downstream synthetic route of [ 23687-26-5 ]

[ 23687-26-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 70538-57-7 ]
  • [ 23687-26-5 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 0.75 h; Microwave irradiation A mixture of 1u (100 mg, 0.81 mmol), hydrazine hydrate (121.5mg, 2.43 mmol), and SS-Rh (370 mg, 2 molpercent Rh) were taken in an oven dried reaction tube equipped with screw cap. 0.5 ml of PEG-400 was added into the reaction mixture. The reaction was then irradiated in a microwave apparatus at 80°C , 80 W for 10 min with a pressure of 80 Psi. After cooling to ambient temperature in the microwave cavity the reaction mixture was extracted with ethyl acetate (3x2 ml) and water (1ml). The combined organic layer wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure and after purificationwith silica gel column chromatography (hexane: EtOAc= 90:10) 2u asyellowish liquid (63 mg, 80percent).1H and 13C NMR spectra hasbeen compared with our previously reported study
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1834 - 1840
[2] Tetrahedron Letters, 2014, vol. 55, # 18, p. 2912 - 2916
[3] Tetrahedron Letters, 2000, vol. 41, # 30, p. 5603 - 5606
[4] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 497,500
[5] Chemistry - A European Journal, 2011, vol. 17, # 21, p. 5903 - 5907
  • 2
  • [ 34784-05-9 ]
  • [ 23687-26-5 ]
YieldReaction ConditionsOperation in experiment
85% With ammonium hydroxide; copper(ll) sulfate pentahydrate In water at 190℃; for 6 h; Reference Example 1
Synthesis of 6-aminoisoquinoline (Reference Compound 1)
6-bromoisoquinoline that weighed 17.2 g (see WO 2008/077553), 200 mL of 28percent ammonia water and 10.8 g of copper (II) sulfate pentahydrate were put into the autoclave and tightly sealed, and the mixture was then stirred at 190° C. for 6 hours.
After cooling to room temperature, the reaction solution was poured into 250 mL of a 10percent aqueous sodium hydroxide solution, followed by extraction with ethyl acetate (100 mL*5).
The extract was dried over anhydrous sodium sulfate, filtered, and then concentrated.
The obtained crude product was suspended in dichloromethane and then filtered to obtain 10.2 g of the compound of interest as a light brown crystal (85percent).
1H-NMR spectrum (CDCl3, δ ppm): 5.54 (br s, 2H), 6.58 (s, 1H), 7.00 (d, J=9.0 Hz, 1H), 7.35 (d, J=5.5 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.98 (s, 1H)
Reference: [1] Patent: US2012/35159, 2012, A1, . Location in patent: Page/Page column 8
  • 3
  • [ 1082674-24-5 ]
  • [ 76144-87-1 ]
  • [ 23687-26-5 ]
YieldReaction ConditionsOperation in experiment
25.4% With tris-(dibenzylideneacetone)dipalladium(0) In dimethyl sulfoxide; ethyl acetate; Petroleum ether Step 3.
Synthesis of 6-amino isoquinoline (#E3).
A solution of #A2 (4.0 g, 51.7 mmol), 6-bromoisoquinoline-1-carbonitrile #A3 (6.0 g, 25.9 mmol), BINAP (3.2 g, 5.2 mmol), Pd2(dba)3 (2.3 g, 2.6 mmol) and potassium phosphate (11.0 g, 51.7 mmol) in anhydrous DMSO (35 mL) was heated at 80° C. for 2 h.
The complete disappearance of the 6-bromoisoquinoline-1-carbonitrile #A3 was observed on TLC.
The reaction mixture was cooled to room temperature, filtered through Celite™ pad and the filtrate was diluted with water (100 mL).
The mixture was extracted with EtOAc (100 mL*3).
The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material which was purified by silica gel (100-200 mesh) column chromatography using 40percent EtOAc in petroleum ether as an eluting system to give #E3 as yellow solid (1.5 g, 25.4percent). Rf: 0.4 (60percent EtOAc in petroleum ether).
LCMS m/z=227.9 (M+H); 1H NMR (400 MHz, d6-DMSO): δ 1.18 (d, J=6.8 Hz, 3H), 3.36-3.47 (m, 1H), 3.48-3.53 (m, 1H), 3.60-3.66 (m, 1H), 6.80-6.82 (m, 2H), 7.32 (dd, J=2.4 Hz, 8.8 Hz, 1H), 7.72 (d, J=5.6 Hz, 1H), 7.87 (d, J=9.6 Hz, 1H), 8.30 (d, J=5.6 Hz, 1H).
24.3% With tris-(dibenzylideneacetone)dipalladium(0) In dimethyl sulfoxide Step 3.
Synthesis of 6-amino isoquinoline (#F3).
A solution of #F2 (4.5 g, 51.7 mmol), 6-bromoisoquinoline-1-carbonitrile (6.0 g, 25.9 mmol), BINAP (3.2 g, 5.1 mmol), Pd2(dba)3 (2.3 g, 2.6 mmol) and potassium phosphate (11.0 g, 51.7 mmol) in anhydrous DMSO (35 mL) was heated at 80° C. for 2 h.
The complete disappearance of the 6-bromoisoquinoline-1-carbonitrile was observed on TLC.
The reaction mixture was cooled to room temperature, filtered through a Celite™ pad and the filtrate was diluted with water (100 mL).
The mixture was extracted with EtOAc (100 mL*3).
The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material.
The product was purified by chromatography on silica gel (100-200 mesh) using 10percent MeOH in DCM as eluant to give racemic #F3 as yellow solid (1.5 g, 24.3percent). Rf: 0.4 (50percent EtOAc in petroleum ether).
Chiral HPLC: two enantiomers (61.0percent, 39.0percent).
LCMS m/z=240.1 (M+H).
H NMR (400 MHz, d6-DMSO): δ 2.19-2.27 (m, 1H), 2.36-2.45 (m, 1H), 3.67-3.84 (m, 3H), 4.02-4.07 (m, 1H), 4.33-4.39 (m, 1H), 5.09 (t, J=4.8 Hz, 1H), 6.83 (d, J=1.6 Hz, 1H), 7.33 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 7.78 (d, J=6.4 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 8.36 (d, J=5.6 Hz, 1H).
Reference: [1] Patent: US2014/155390, 2014, A1, . Location in patent: Page/Page column
[2] Patent: US2014/155390, 2014, A1, . Location in patent: Page/Page column
  • 4
  • [ 7651-82-3 ]
  • [ 1336-21-6 ]
  • [ 23687-26-5 ]
Reference: [1] Patent: US4812573, 1989, A,
  • 5
  • [ 7651-82-3 ]
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Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 4997
  • 6
  • [ 39585-32-5 ]
  • [ 23687-26-5 ]
Reference: [1] Patent: US9840468, 2017, B1,
  • 7
  • [ 99-60-5 ]
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Reference: [1] Patent: US9840468, 2017, B1,
  • 8
  • [ 52962-35-3 ]
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Reference: [1] Patent: US9840468, 2017, B1,
  • 9
  • [ 91-21-4 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 497,500
  • 10
  • [ 23687-26-5 ]
  • [ 566943-98-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1345 - 1348
[2] Patent: WO2012/595, 2012, A1, . Location in patent: Page/Page column 117
[3] Patent: US2013/102603, 2013, A1, . Location in patent: Paragraph 0522; 0523
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