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Chemical Structure| 27104-73-0
Chemical Structure| 27104-73-0
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Product Details of [ 27104-73-0 ]

CAS No. :27104-73-0 MDL No. :MFCD00075138
Formula : C11H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZBCGBIZQNMVMPC-UHFFFAOYSA-N
M.W : 187.20 Pubchem ID :725374
Synonyms :

Calculated chemistry of [ 27104-73-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.02
TPSA : 39.19 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) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.29
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.36
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 1.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.84
Solubility : 0.271 mg/ml ; 0.00145 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.332 mg/ml ; 0.00178 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0312 mg/ml ; 0.000167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 27104-73-0 ]

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 [ 27104-73-0 ]

* 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 [ 27104-73-0 ]
  • Downstream synthetic route of [ 27104-73-0 ]

[ 27104-73-0 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 27104-73-0 ]
  • [ 5470-80-4 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With diisobutylaluminium hydride In toluene at -78℃; for 0.25 h;
Stage #2: With water; acetic acid In diethyl ether; toluene at -78 - 20℃;
Isoquinoline-3-carbaldehyde; A solution of methyl 3-isoquinolinecarboxylate (2. 0 g, 10.7 mmol) in toluene was cooled to-78°C. To the solution was added diisobutylaluminum hydride (1M in toluene, 21.4 mL, 21.4 mmol) slowly over 15 minutes via syringe. While still at-78°C, the reaction was quenched with a solution of ether (80 mL), acetic acid (20 mL) and water (8 mL) and then the mixture was allowed to slowly warm to room temperature overnight. The organics were decanted and the solvent was evaporated. Flash column chromatography (gradient 1: 4 ethyl acetate/hexanes to 1: 3 ethyl acetate/hexanes) provided 1.1 grams of the title compound (65percent yield).'H-NMR (CDC13, 300 MHz) 8 10.24 (s, 1H), 9.35 (s, 1H), 8.36 (s, 1H), 8.07-7. 98 (m, 2H), 7.82-7. 32 (m, 2H). Mass spec.: 158 (MH) +.
54% With diisobutylaluminium hydride In tetrahydrofuran at 0℃; for 2 h; To a cooled solution 0°C of isoquinoline-3-carboxylic acid methyl ester (l. Og, 5.34mmol) in anhydrous tetrahydrofuran (100ml), is added a solution of DIBAL-H (11. 8ml, 11. 8mmol). The reaction mixture is stirred at 0°C for 2 hours and then quenched with saturated aqueous sodium potassium tartrate and stirred for 2 hours. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed with 1N HCl, 2N NaOH, and dried over anhydrous Na2S04, filtered, and concentrated ira vacuo. The crude reaction mixture is purified on silica gel eluting with 20percent ethyl acetate/hexanes to give isoquinoline-3-carboxaldehyde (0.46g, 54percent).'H NMR (CDC13) : 8 = 10.24 (1H, brs), 9.32 (1H, brs), 8.35 (1H, brs), 8. 02 (2H, brd), 7.77 (2H, brs).
33%
Stage #1: With diisobutylaluminium hydride In toluene at 0 - 10℃; for 3 h;
Stage #2: With water; Rochelle's salt In toluene for 0.25 h;
Example 11;: 3-Amino-6- [4- (2-hydroxy-2-isoquinolin-3-yl-ethylamino)-piperidin-1-yl]- 4-propyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide Methyl 3-isoquinoline carboxylate (1.50 g, 8.01 mmol) was placed in 60 mL anhydrous toluene and cooled to 0 °C. The solution was treated dropwise with 1M DIBAL solution in toluene (8.2 mL, 8.2 mmol). The solution gradually changed from colorless to yellow and then orange during addition. After 2 h another 2 mL 1M DIBAL solution in toluene was added and the mixture was left stirring another 1 h at 0-10 °C. The mixture was then quenched with aqueous Na K tartrate solution, stirred 15 min then diluted with brine and EtOAc. The layers were separated and the aqueous was extracted twice with EtOAc. The combined organics were washed with brine repeatedly (emulsion), dried (MgS04), filtered and the solvent was removed in vacuo. An orange oil was thus obtained, which was purified by flash column chromatography on Si02 using CH2Cl2/MeOH eluent mixtures. The desired isoquinoline carboxaldehyde was isolated as a yellow solid, 420 mg (33percent of theory).
Reference: [1] Patent: WO2005/56550, 2005, A2, . Location in patent: Page/Page column 75-76
[2] Patent: WO2005/92885, 2005, A1, . Location in patent: Page/Page column 73
[3] Patent: WO2005/56562, 2005, A1, . Location in patent: Page/Page column 71-72
[4] Tetrahedron Letters, 1999, vol. 40, # 6, p. 1211 - 1214
[5] Patent: US5554620, 1996, A,
  • 2
  • [ 27104-73-0 ]
  • [ 26947-41-1 ]
Reference: [1] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
  • 3
  • [ 27104-73-0 ]
  • [ 6624-49-3 ]
YieldReaction ConditionsOperation in experiment
60.69% With sodium hydroxide In methanolCooling with ice Add to 100ml eggplantIsoquinoline-3-carboxylate (3) (858 mg, 4.59 mmol)With a small amount of methanol dissolved, ice salt bath with 2N NaOH to adjust the pH = 12, a white precipitate;After the reaction is over,Ice salt bath with saturated KHSO4 adjusted pH = 7,Remove all solvents.The mixture was dissolved in a mixed solution of dichloromethane and methanol, and the filtrate was collected by filtration.After the filtrate was removed,A white solid (481.7 mg, 60.69percent) was obtained.
Reference: [1] Patent: CN106986825, 2017, A, . Location in patent: Paragraph 0023; 0033; 0034
[2] Patent: CN107137355, 2017, A, . Location in patent: Paragraph 0088; 0089
[3] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965
  • 4
  • [ 27104-73-0 ]
  • [ 50458-77-0 ]
Reference: [1] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
[2] Journal of Organic Chemistry, 2009, vol. 74, # 3, p. 1171 - 1178
  • 5
  • [ 57060-86-3 ]
  • [ 27104-73-0 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4642 - 4643
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5469 - 5475
[3] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1081 - 1091
[4] Heterocycles, 1982, vol. 19, # 6, p. 1003 - 1007
[5] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
[6] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3978 - 3981
[7] Patent: CN107137355, 2017, A, . Location in patent: Paragraph 0088; 0089
  • 6
  • [ 79815-19-3 ]
  • [ 27104-73-0 ]
YieldReaction ConditionsOperation in experiment
24.56% With potassium permanganate In N,N-dimethyl-formamide for 6 h; Add to 250ml eggplant(3S) -1,2,3,4-tetrahydroisoquinoline-3-carboxylate (2) (4.23 g, 22.15 mmol)The solution was dissolved by adding N, N-dimethylformamide (50 ml)Potassium permanganate (2.97 g, 18.79 mmol)The reaction was added after 6 hEthanol (50 ml) was stirred for 30 min,Remove the solvent, add methanol (30ml) re-dissolved.The residue was purified by column chromatography to give a colorless solid (858 mg, 24.56percent).
Reference: [1] RSC Advances, 2017, vol. 7, # 77, p. 48848 - 48852
[2] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965
[3] Patent: CN106986825, 2017, A, . Location in patent: Paragraph 0023; 0031; 0032
  • 7
  • [ 67-56-1 ]
  • [ 6624-49-3 ]
  • [ 27104-73-0 ]
YieldReaction ConditionsOperation in experiment
75% Reflux The compound 3-isoquinolinecarboxylic acid (0801-132) (1.0 g, 5.78 mmol, 1.0 eq.)Dissolved in 30 ml of methanol,Sulfuric acid (0.5 ml) was then added and the reaction was refluxed overnight.After the reaction is finished, add sodium bicarbonate solutionpH to 8, extracted with dichloromethane, liquid-separated, and the organic phase dried over anhydrous sodium sulfate.Spin-drying afforded the compound 3-isoquinolinecarboxylic acid methyl ester (810 mg, 75percent).
Reference: [1] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0383
  • 8
  • [ 89524-99-2 ]
  • [ 643-79-8 ]
  • [ 27104-73-0 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 45, p. 7935 - 7938
  • 9
  • [ 67123-97-1 ]
  • [ 27104-73-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3978 - 3981
[2] Organic Preparations and Procedures International, 1994, vol. 26, # 4, p. 429 - 438
[3] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1081 - 1091
[4] Patent: CN107137355, 2017, A,
  • 10
  • [ 44804-84-4 ]
  • [ 88284-48-4 ]
  • [ 1046475-28-8 ]
  • [ 27104-73-0 ]
Reference: [1] Synlett, 2008, # 8, p. 1159 - 1164
  • 11
  • [ 35356-70-8 ]
  • [ 26260-02-6 ]
  • [ 27104-73-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 29, p. 5079 - 5081
  • 12
  • [ 2495-35-4 ]
  • [ 57060-86-3 ]
  • [ 27104-73-0 ]
Reference: [1] Synlett, 2009, # 1, p. 97 - 99
  • 13
  • [ 57060-86-3 ]
  • [ 27104-73-0 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5469 - 5475
  • 14
  • [ 5429-56-1 ]
  • [ 124-41-4 ]
  • [ 6630-33-7 ]
  • [ 27104-73-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 6011 - 6019
  • 15
  • [ 79815-19-3 ]
  • [ 27104-73-0 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 77, p. 48848 - 48852
  • 16
  • [ 63-91-2 ]
  • [ 27104-73-0 ]
Reference: [1] Patent: CN106986825, 2017, A,
[2] Patent: CN107137355, 2017, A,
[3] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965
  • 17
  • [ 59259-01-7 ]
  • [ 27104-73-0 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1984, # 12, p. 776 - 777
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 921 - 926
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 921 - 926
  • 18
  • [ 150-30-1 ]
  • [ 27104-73-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3978 - 3981
  • 19
  • [ 74163-81-8 ]
  • [ 27104-73-0 ]
Reference: [1] Patent: CN106986825, 2017, A,
[2] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965
  • 20
  • [ 34824-58-3 ]
  • [ 27104-73-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 921 - 926
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 921 - 926
  • 21
  • [ 5535-48-8 ]
  • [ 57060-86-3 ]
  • [ 27104-73-0 ]
Reference: [1] Synlett, 2009, # 1, p. 97 - 99
  • 22
  • [ 124300-67-0 ]
  • [ 124300-75-0 ]
  • [ 124300-76-1 ]
  • [ 134272-14-3 ]
  • [ 27104-73-0 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 11, p. 1409 - 1412
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