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[ CAS No. 34846-65-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 34846-65-6
Chemical Structure| 34846-65-6
Chemical Structure| 34846-65-6
Structure of 34846-65-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 34846-65-6 ]

CAS No. :34846-65-6 MDL No. :MFCD00957039
Formula : C10H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NPDZTCFGRSYTPF-UHFFFAOYSA-N
M.W : 154.17 Pubchem ID :96450
Synonyms :

Calculated chemistry of [ 34846-65-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.46
TPSA : 36.68 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.425 mg/ml ; 0.00276 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 0.95 mg/ml ; 0.00616 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0261 mg/ml ; 0.000169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 34846-65-6 ]

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

Application In Synthesis of [ 34846-65-6 ]

* 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 [ 34846-65-6 ]
  • Downstream synthetic route of [ 34846-65-6 ]

[ 34846-65-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 557-21-1 ]
  • [ 34784-02-6 ]
  • [ 34846-65-6 ]
YieldReaction ConditionsOperation in experiment
27.4% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 120℃; Inert atmosphere To a stirred solution of 3-bromoisoquinoline (Intermediate-12) (9.2 g, 44.2 mmol) in DMF (15 mL) were added, Pd(PPh3)4 (10.2 g, 8.84 mmol) and Zn(CN)2 (10.34 g, 88.44 mmol, 2.0 eq) and the solution was degassed with N2 for 20 min. It was then heated to 120° C. overnight. After the completion (TLC), reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (10percent EtOAc:Hexanes) to afford the desired compound (3.4 g, 27.4percent) as pale yellow solid
Reference: [1] Patent: US2013/178457, 2013, A1, . Location in patent: Paragraph 0220
  • 2
  • [ 557-21-1 ]
  • [ 1532-97-4 ]
  • [ 34846-65-6 ]
YieldReaction ConditionsOperation in experiment
27.4% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 120℃; Inert atmosphere lntermediate-13: lsoquinolin-4-carbonitrile: To a stirred solution of 3-bromoisoquinoline (lntermediate-12) (9.2 g, 44.2 mmol) in DMF (15 mL) were added, Pd(PPh3)4 (10.2 g, 8.84 mmol) and Zn(CN)2 (10.34 g, 88.44 mmol, 2.0 eq) and the solution was degassed with N2 for 20 min. It was then heated to 120 2C overnight. After the completion (TLC), reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (10percent EtOAc:Hexanes) to afford the desired compound (3.4 g, 27.4percent) as pale yellow solid.
Reference: [1] Patent: WO2013/5168, 2013, A2, . Location in patent: Page/Page column 40
  • 3
  • [ 1532-97-4 ]
  • [ 544-92-3 ]
  • [ 34846-65-6 ]
YieldReaction ConditionsOperation in experiment
58% at 150 - 230℃; Example 64: Synthesis of 4-(3-(2-fluoro-4-methoxybenzylidene)-3 ,4,5,6- 5 tetrahydropyridin-2-yl)isoquinoline dihydrochloride.; The preparation of 4-(3-(2-fluoro-4-methoxybenzylidene)-3,4,5,6- tetrahydropyridin-2-yl)isoquinoline dihydrochloride is described below.; A. Step 1: Preparation of Intermediate 9; Intermediate 9 was prepared as described in Tyson, F.T. J. Am. Chem. Soc, 1939, 61 (I )5 183 -185. Briefly, 4-Bromoisoquinoline (3.36 g, 16.2 mmol) and Cu(I)CN (2.17 g, 24.2 mmol) were combined as the dry solids in a round bottom flask fitted with a magnetic stirrer and vigeraux column under N2. Heat was applied.15 At approximately 1500C, the mixture began to stir freely. At approximately 23O0C, the reaction mixture formed a black solid that began to splatter onto the sides of the flask. The reaction was cooled to room temperature and treated with concentrated NH4OH overnight. This mixture was then extracted 3 times with EtOAc. The EtOAc extracts were washed with dilute NH4OH(Hq) and brine, then combined, dried 0 over Na2SO4, treated with decolorizing charcoal, filtered through celite, then concentrated under reduced pressure. The recovered material was dissolved into a mixture of hot isopropanol and methanol to re-crystallize. The crystals were recovered by vacuum filtration, washed with fresh isopropanol and dried under vacuum giving 1.47 g (58percent) of yellow crystals. LC-MS: RT = 7.86 min, [M+H]+ = 5 155.1.
Reference: [1] Synthetic Communications, 2004, vol. 34, # 1, p. 137 - 149
[2] Patent: WO2007/89626, 2007, A2, . Location in patent: Page/Page column 71
[3] Archiv der Pharmazie, 1993, vol. 326, # 10, p. 785 - 790
[4] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263
  • 4
  • [ 1532-97-4 ]
  • [ 34846-65-6 ]
YieldReaction ConditionsOperation in experiment
44.6% at 250℃; for 0.75 h; To 4-bromo isoquinoline (2 g, 9.613 mmol) is added copper (I) cyanide (1.29 g, 14.42 mmol), and the mixture is heated to 250° C. for 45 minutes, where the pressure is taken down to 5-10 torr.
The mixture which turns black at this point begins to distil over, giving crystals in the condenser.
The condenser is cleaned with dichloromethane and the volatiles in the solution are removed in vacuo to give the desired product (0.66 g, 44.6percent) as colorless crystals.
Reference: [1] Patent: US2006/276515, 2006, A1, . Location in patent: Page/Page column 44
  • 5
  • [ 78593-42-7 ]
  • [ 34846-65-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 860 - 863
  • 6
  • [ 1532-91-8 ]
  • [ 557-21-1 ]
  • [ 34846-65-6 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3303 - 3305
  • 7
  • [ 1532-97-4 ]
  • [ 557-21-1 ]
  • [ 34846-65-6 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3303 - 3305
  • 8
  • [ 1532-97-4 ]
  • [ 75-86-5 ]
  • [ 34846-65-6 ]
Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1540 - 1545
  • 9
  • [ 1532-97-4 ]
  • [ 34846-65-6 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 21, p. 6249 - 6254
  • 10
  • [ 1532-97-4 ]
  • [ 34846-65-6 ]
Reference: [1] Synlett, 2007, # 4, p. 555 - 558
[2] Synthesis, 2008, # 20, p. 3351 - 3355
  • 11
  • [ 119-65-3 ]
  • [ 34846-65-6 ]
Reference: [1] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263
[2] Patent: US2013/178457, 2013, A1,
[3] Patent: WO2013/5168, 2013, A2,
  • 12
  • [ 1532-97-4 ]
  • [ 34846-65-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 860 - 863
  • 13
  • [ 75-05-8 ]
  • [ 192182-56-2 ]
  • [ 34846-65-6 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13246 - 13252
  • 14
  • [ 100-52-7 ]
  • [ 117908-22-2 ]
  • [ 34846-65-6 ]
  • [ 1459-20-7 ]
  • [ 117908-29-9 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1988, vol. 36, # 3, p. 930 - 939
  • 15
  • [ 34846-65-6 ]
  • [ 7159-36-6 ]
YieldReaction ConditionsOperation in experiment
59.3% With water; potassium hydroxide In ethanolReflux To a stirred solution of isoquinolin-4-carbonitrile (Intermediate-13) (3.0 g, 19.45 mmol) in EtOH (30 mL) was added KOH (20 g in 20 mL water) and the mixture was refluxed overnight. It was then cooled to RT and concentrated under reduced pressure. The aqueous layer was washed with Et2O and neutralized using 1N HCl. It was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound (2 g, 59.3percent) as an off white solid.
59.3% Reflux lntermediate-14: lsoquinolin-4-carboxylic acid: To a stirred solution of isoquinolin-4-carbonitrile (lntermediate-13) (3.0 g, 19.45 mmol) in EtOH (30 mL) was added KOH (20 g in 20 mL water) and the mixture was refluxed overnight. It was then cooled to RT and concentrated under reduced pressure. The aqueous layer was washed with Et20 and neutralized using 1 N HCI. It was extracted with EtOAc and the organic layer was dried over Na2S04, filtered, and concentrated to give the title compound (2 g, 59.3percent) as an off white solid.
Reference: [1] Patent: US2013/178457, 2013, A1, . Location in patent: Paragraph 0221
[2] Patent: WO2013/5168, 2013, A2, . Location in patent: Page/Page column 40
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 3030
[4] Journal of the American Chemical Society, 1939, vol. 61, p. 183
[5] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263
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