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[ CAS No. 7742-73-6 ] {[proInfo.proName]}

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Chemical Structure| 7742-73-6
Chemical Structure| 7742-73-6
Structure of 7742-73-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7742-73-6 ]

CAS No. :7742-73-6 MDL No. :MFCD00034750
Formula : C9H5Cl2N Boiling Point : -
Linear Structure Formula :- InChI Key :BRGZEQXWZWBPJH-UHFFFAOYSA-N
M.W : 198.05 Pubchem ID :298625
Synonyms :

Calculated chemistry of [ 7742-73-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.76
TPSA : 12.89 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) : -4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 4.02
Log Po/w (WLOGP) : 3.54
Log Po/w (MLOGP) : 2.98
Log Po/w (SILICOS-IT) : 3.72
Consensus Log Po/w : 3.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.012 mg/ml ; 0.0000607 mol/l
Class : Moderately soluble
Log S (Ali) : -3.99
Solubility : 0.0201 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.94
Solubility : 0.00229 mg/ml ; 0.0000116 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.53

Safety of [ 7742-73-6 ]

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 [ 7742-73-6 ]

* 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 [ 7742-73-6 ]
  • Downstream synthetic route of [ 7742-73-6 ]

[ 7742-73-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 7742-73-6 ]
  • [ 19493-45-9 ]
YieldReaction ConditionsOperation in experiment
24% With phosphorus; hydrogen iodide In water; acetic acid for 24 h; Reflux A mixture of 1,3-dichloroisoquinoline (5.00 g, 25.2 mmol), red phosphorus, (1.72 g, 55.5 mmol), and hydriodic acid (10.5 mL, 58.1 mmol) in acetic acid (25 mL) was heated to reflux for 24 hours. The reaction mixture was cooled and poured onto ice, and the resulting solution brought to pΗ 7 by the addition of ION aqueous sodium hydroxide. The solution was extracted with dichloromethane (2 x 50 mL), and the organic layers concentrated. The residue was purified by silica gel chromatography (elution with 10percentEtOAc/hexanes) to provide 1.01 g (24percent) of the title compound. MS (DCIZNH3) mZz 164 (M+H)+.
24% With phosphorus; hydrogen iodide In water; acetic acid for 24 h; Reflux A mixture of 1,3-dichloroisoquinoline (5.00 g, 25.2 mmol), red phosphorus, (1.72 g, 55.5 mmol), and hydriodic acid (10.5 mL, 58.1 mmol) in acetic acid (25 mL) was heated to reflux for 24 hours. The reaction mixture was cooled and poured onto ice, and the resulting solution brought to pΗ 7 by the addition of ION aqueous sodium hydroxide. The solution was extracted with dichloromethane (2 x 50 mL), and the organic layers concentrated. The residue was purified by silica gel chromatography (elution with 10percentEtOAc/hexanes) to provide 1.01 g (24percent) of the title compound. MS (DCIZNH3) mZz 164 (M+H)+.
23%
Stage #1: With hydrogenchloride; tin; acetic acid In water at 55 - 60℃; for 3 h;
Stage #2: With ammonia In water
EXAMPLE 60C
3-chloroisoquinoline
The product from Example 60B (6.73 g, 33.8 mmol) was suspended in glacial acetic acid (37 mL) and concentrated HCl (13 mL), treated with tin powder (12.1 g, 101.9 mmol), and heated at 55-60° C. for 3 hours with stirring.
The mixture was allowed to cool to room temperature and the precipitated tin salts were removed by filtration through Celite.
The filtrate was basified to pH 9 with concentrated NH4OH and then extracted with ethyl acetate.
The organic extracts were combined, washed with saturated NaHCO3 solution, dried over Na2SO4, and concentrated under reduced pressure to provide the title compound as a gummy yellow residue (1.28 g, 23percent).
Reference: [1] Patent: WO2010/45401, 2010, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2010/45402, 2010, A1, . Location in patent: Page/Page column 87
[3] Patent: US2005/113576, 2005, A1, . Location in patent: Page/Page column 30
[4] Chemische Berichte, 1886, vol. 19, p. 1655,2356
[5] Chemische Berichte, 1886, vol. 19, p. 1655,2356
[6] Journal of the Chemical Society, 1948, p. 777,781
[7] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[8] Patent: US4409017, 1983, A,
[9] Patent: WO2010/127855, 2010, A1, . Location in patent: Page/Page column 136; 137
  • 2
  • [ 7742-73-6 ]
  • [ 119-65-3 ]
  • [ 19493-45-9 ]
YieldReaction ConditionsOperation in experiment
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 2.5 h; Inert atmosphere General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 molpercent), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
  • 3
  • [ 7742-73-6 ]
  • [ 7440-31-5 ]
  • [ 19493-45-9 ]
Reference: [1] Patent: US2003/158188, 2003, A1,
[2] Patent: US6933311, 2005, B2,
[3] Patent: US2004/157849, 2004, A1,
  • 4
  • [ 7742-73-6 ]
  • [ 58022-21-2 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 13, p. 2507 - 2514
  • 5
  • [ 4456-77-3 ]
  • [ 7742-73-6 ]
YieldReaction ConditionsOperation in experiment
74% With P,P-dichlorophenylphosphine oxide In tetrahydrofuran; water at 20 - 160℃; EXAMPLE 60B
1,3-dichloroisoquinoline
The product from Example 60A (6.5 g, 40.4 mmol) was treated with phenylphosphonic dichloride (11.5 mL, 81.1 mmol) and heated at 160° C. for 3 hours.
The reaction was allowed to cool to room temperature and stand overnight.
The resulting waxy orange material was dissolved in tetrahydrofuran (200 mL), treated with water (60 mL), and then concentrated under reduced to remove the tetrahydrofuran.
The remaining aqueous material was neutralized with concentrated NH4OH and extracted with ethyl acetate.
The ethyl acetate phases were combined, washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure to provide the title compound as yellow flakes (6.92 g, 74percent).
Reference: [1] Patent: US2005/113576, 2005, A1, . Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[3] Patent: US6340759, 2002, B1, . Location in patent: Example 17
[4] Patent: WO2010/127855, 2010, A1, . Location in patent: Page/Page column 136; 137
  • 6
  • [ 6627-91-4 ]
  • [ 7742-73-6 ]
YieldReaction ConditionsOperation in experiment
84.5% With phosphorus pentachloride; trichlorophosphate In 2-cyanomethylbenzoic acid at 20 - 70℃; for 17.5 h; 16.2 Preparation of 1,3-dichloroisoquinoline
1.3 g (6.24 mmol) of phosphorus pentachloride were dissolved in 6 ml of phosphoryl chloride and admixed with 1.0 g (6.21 mmol) of o-cyanomethylbenzoic acid from example 16.1 in portions.After stirring at room temperature for 90 min, all had dissolved, and the solution was heated to 70° C. for 16 h.After the mixture had been cooled, it was poured cautiously onto 50 g of ice and admixed with 50 ml of ethyl acetate.The phases were separated and the aqueous phase was extracted twice with 50 ml each time of acetic acid.The combined organic phases were washed with 50 ml of H2O and 50 ml of saturated NaHCO3 solution, and dried over MgSO4, and the solvent was removed under reduced pressure.The brown, crystalline crude product was purified by filtering together with dichloromethane/cyclohexane (1:1) through a short silica gel column (2*15 cm).1.04 g (5.25 mmol, 84.5percent) of 1,3-dichloroisoquinoline were obtained.
Reference: [1] Patent: US2004/199024, 2004, A1, . Location in patent: Page 19
  • 7
  • [ 824-72-6 ]
  • [ 4456-77-3 ]
  • [ 7742-73-6 ]
Reference: [1] Patent: US6933311, 2005, B2,
[2] Patent: US2004/157849, 2004, A1,
  • 8
  • [ 86-94-2 ]
  • [ 7742-73-6 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 5481
  • 9
  • [ 824-72-6 ]
  • [ 7742-73-6 ]
Reference: [1] Patent: US2003/158188, 2003, A1,
  • 10
  • [ 13331-23-2 ]
  • [ 1168136-15-9 ]
  • [ 7742-73-6 ]
  • [ 1168136-22-8 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 25, p. 3081 - 3083
  • 11
  • [ 89-51-0 ]
  • [ 7742-73-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
  • 12
  • [ 53558-67-1 ]
  • [ 10025-87-3 ]
  • [ 7742-73-6 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1720
  • 13
  • [ 7742-73-6 ]
  • [ 58142-49-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[2] Patent: US2004/157849, 2004, A1,
  • 14
  • [ 7742-73-6 ]
  • [ 7574-67-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8603 - 8614
  • 15
  • [ 7742-73-6 ]
  • [ 205264-33-1 ]
Reference: [1] Patent: US6169088, 2001, A,
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