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[ CAS No. 799293-85-9 ] {[proInfo.proName]}

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Chemical Structure| 799293-85-9
Chemical Structure| 799293-85-9
Structure of 799293-85-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 799293-85-9 ]

CAS No. :799293-85-9 MDL No. :MFCD08275115
Formula : C7H5BrN2S Boiling Point : -
Linear Structure Formula :- InChI Key :NRVPVUKWJYSNTO-UHFFFAOYSA-N
M.W : 229.10 Pubchem ID :18450797
Synonyms :

Calculated chemistry of [ 799293-85-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.72
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.26
Solubility : 0.126 mg/ml ; 0.000552 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.127 mg/ml ; 0.000556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.0776 mg/ml ; 0.000339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 799293-85-9 ]

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 [ 799293-85-9 ]

* 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 [ 799293-85-9 ]
  • Downstream synthetic route of [ 799293-85-9 ]

[ 799293-85-9 ] Synthesis Path-Upstream   1~9

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Reference: [1] Patent: US2005/26944, 2005, A1,
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YieldReaction ConditionsOperation in experiment
94% With ammonia In 1,4-dioxane; water at 150℃; for 18 h; A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150 C. The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94percent) of the desired product. 1H NMR (DMSO-d6, 400 MHz) ? 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.
94% With ammonia In 1,4-dioxane; water at 150℃; for 18 h; EXAMPLE 219A
3-bromothieno[3,2-c]pyridin-4-amine
A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150° C.
The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate.
The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94percent) of the desired product. 1H NMR (DMSO-d6, 400 MHz) δ 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.
84 mg With ammonium chloride In 1-methyl-pyrrolidin-2-one at 150℃; for 3 h; Microwave irradiation 3-Bromo-4-chloro-thieno[3,2-c]pyridine (300 mg, 1.21 mmol) was dissolved in NMP (3 mL) and placed in a 20-mL microwave vial. A saturated solution of NH4CI (5 mL) was added to the vial and the mixture was microwave heated at 150 °C for a total time of 3 h. The mixture was then diluted with water and extracted with ethyl acetate. The aqueous solution was then basified with NaOH and extracted with AcOEt. The latter solution was dried with Na2S04 and evaporated to dryness. The residue was purified by flash column chromatography over silica gel eluting with DCM to yield 3-bromo-thieno[3,2-c]pyridin-4-ylamine (84 mg). HPLC (254 nm): Rt: 4.38 min. HRMS (ESI) calcd for C7H5BrN2S [M+H]+ 228.9430, found 228.9441. 1 H NMR (500 MHz, DMSO-d6) delta ppm: 6.49 (s, 2 H) 7.27 (d, J=5.64 Hz, 1 H) 7.78 (s, 1 H) 7.83 (d, J=5.64 Hz, 1 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1167 - 1171
[2] Patent: US2005/20619, 2005, A1, . Location in patent: Page 47
[3] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 56
[4] Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3849 - 3855
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1246 - 1249
[7] Patent: WO2004/100947, 2004, A2, . Location in patent: Page 27; 17
[8] Patent: US2005/20619, 2005, A1, . Location in patent: Page 17
[9] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 26
[10] Patent: WO2017/220477, 2017, A1, . Location in patent: Page/Page column 28-29
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Reference: [1] Patent: US2005/26944, 2005, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1167 - 1171
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
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Reference: [1] Patent: US2005/26944, 2005, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1246 - 1249
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
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