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[ CAS No. 22034-13-5 ] {[proInfo.proName]}

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Chemical Structure| 22034-13-5
Chemical Structure| 22034-13-5
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Product Details of [ 22034-13-5 ]

CAS No. :22034-13-5 MDL No. :MFCD00614355
Formula : C6H3BrN2S Boiling Point : -
Linear Structure Formula :- InChI Key :KYKBVPGDKGABHY-UHFFFAOYSA-N
M.W : 215.07 Pubchem ID :736492
Synonyms :

Calculated chemistry of [ 22034-13-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.11
TPSA : 54.02 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) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.48
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 2.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0853 mg/ml ; 0.000396 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.118 mg/ml ; 0.000551 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.0753 mg/ml ; 0.00035 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 22034-13-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22034-13-5 ]

* 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 [ 22034-13-5 ]
  • Downstream synthetic route of [ 22034-13-5 ]

[ 22034-13-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 22034-13-5 ]
  • [ 15155-41-6 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 4, p. 1566 - 1573
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1973, vol. 9, p. 293 - 295[3] Khimiya Geterotsiklicheskikh Soedinenii, 1973, vol. 9, # 3, p. 319 - 321
  • 2
  • [ 273-13-2 ]
  • [ 22034-13-5 ]
YieldReaction ConditionsOperation in experiment
49% With hydrogen bromide; bromine In water at 100℃; for 9 h; To a flask equipped with a reflux device, 25.0 g (183.7 mmol) of the compound (a), and 150 mL of 48percent hydrobromic acid were added. After heating to 100° C., 8.5 mL (165.4 mmol) of bromine was dropped, the resultant was stirred at 100° C. for nine hours, and then it was let cool. After a reaction was finished, 200 mL of dichloromethane was added, precipitated solid was dissolved, and further 100 mL of an aqueous sodium sulfate solution was added. An organic layer was collected, washed with a saturated aqueous sodium hydrogen carbonate solution, dried with anhydrous sodium sulfate, and then a solvent was removed under reduced pressure to obtain an unrefined compound (b). The compound (b) was suspended in 200 mL of hexane/ethyl acetate (4:1, volume ratio), remaining solids were filtered to thereby remove 4,7-dibromo-2,1,3-benzothiadiazole being a by-product. The filtrate was condensed again, suspended in 200 mL of hexane, and remaining solids were filtered, to thereby obtain 11.2 g of the compound (b). Further, the filtrate was condensed, and refinement was performed by a column chromatography method using hexane/ethyl acetate (97:3, volume ratio) as a developing solution, to thereby obtain 8.0 g of the compound (b). A sum total was 19.2 g (89.3 mmol), and a yield was 49percent.
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15189 - 15193[2] Angew. Chem., 2018, vol. 130, p. 15409 - 15413,5
[3] Chemical Communications, 2013, vol. 49, # 39, p. 4304 - 4306
[4] Journal of Physical Chemistry B, 2012, vol. 116, # 24, p. 7259 - 7268
[5] Patent: US2018/346729, 2018, A1, . Location in patent: Paragraph 0181; 0182
[6] RSC Advances, 2018, vol. 8, # 58, p. 33276 - 33290
[7] New Journal of Chemistry, 2017, vol. 41, # 4, p. 1566 - 1573
[8] Inorganic Chemistry, 2014, vol. 53, # 12, p. 6204 - 6223
[9] Chemical Communications, 2012, vol. 48, # 4, p. 573 - 575
[10] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633
[11] Patent: CN106588935, 2017, A, . Location in patent: Paragraph 0053; 0054
  • 3
  • [ 95-54-5 ]
  • [ 22034-13-5 ]
Reference: [1] Journal of Physical Chemistry B, 2012, vol. 116, # 24, p. 7259 - 7268
  • 4
  • [ 767-64-6 ]
  • [ 22034-13-5 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 1714 - 1719[2] Zhurnal Obshchei Khimii, 1963, vol. 33, # 6, p. 1759 - 1766
  • 5
  • [ 22034-13-5 ]
  • [ 1575-36-6 ]
YieldReaction ConditionsOperation in experiment
92% With sodium tetrahydroborate In ethanol at 20℃; for 16 h; 2000mL 1-neck flask (one neck flask) for 4-bromo-benzo [c] [1,2,5] thiadiazole (10g, 46.5 mmol), NaBH4 (17.6g, 465 mmol) were placed into a 900mL EtOH after stirring at room temperature for 16 hours. When the reaction is complete, remove the solvents by rotary evaporation the drier and extracted with CHCl3. Thus extracted organic layer was washed with brine solution. Thereafter, the dried organic layer was again put on MgSO4 and the solvent removed by evaporation dryer to give the title compound C-2-1 (8.0g, 47.6 mmol, 92percent).
81%
Stage #1: With sodium tetrahydroborate; cobalt(II) chloride hexahydrate In methanol for 3 h; Reflux
Example 8: N,N-dimethyl-3-(3-(2-oxo-2,3-dihydro-1 H-benzo[d]imidazol-4-yl)-2- (pyridin-4-yl)pyrazolo[1 ,5-a]pyrimidin-7-yl)benzene-sulfonamide <n="33"/> Step 1 : 3-Bromo-benzene-1 ,2-diamine To a solution of 4-bromo-benzo[1 ,2,5]thiadiazole (1.15g, 5.35 mmol) in methanol (10 ml_) was added sodium borohydride (203 mg, 5.35 mmol) and cobalt chloride hexahydrate (120 mg, 0.533 mmol). The mixture was refluxed for 3 hours, cooled to room temperature and then filtered to remove the black solid. The solvent was evaporated, water (100 ml_) was added and the product was extracted with Et2O (3 x, 30 mL). The combined organic extracts were dried over Na24 and the solvent removed, resulting in the air-unstable 3-bromo-benzene-1 ,2- diamine (810 mg, 81percent yield). MS: 187.0 [M+H].
81% With sodium tetrahydroborate; cobalt(II) chloride hexahydrate In methanol for 3 h; Reflux Example 83: Ethyl 3-[3-(2-oxo-2,3-dihydro-1 H-benzimidazol-4-yl)-2-pyridin-4- ylpyrazolo[1 ,5-a]pyrimidin-7-yl]-8-azabicyclo[3.2.1]octane-8-carboxylate; <n="98"/> Step 1 : To a solution of 4-bromo-benzo[1 ,2,5]thiadiazole (1.15g, 5.35 mmol) in methanol (10 ml.) was added sodium borohydride (203 mg, 5.35 mmol) and cobalt(ll) chloride hexahydrate (120 mg, 0.533 mmol). The mixture was refluxed for 3 hours, then cooled to room temperature and filtered to remove the black solid. The solvent was evaporated, water (100 ml.) was added and the mixture was extracted with ether (3 x 30 ml_). The combined organic extracts were dried over sodium sulfate, filtered, and then concentrated in-vacuo, to provide 3-bromo-benzene-1 ,2-diamine (810 mg, 81 percent yield). MS: 187.0 [M+H].
Reference: [1] Patent: KR101612903, 2016, B1, . Location in patent: Paragraph 0110-0112
[2] Journal of Physical Chemistry B, 2012, vol. 116, # 24, p. 7259 - 7268
[3] Patent: WO2009/111260, 2009, A1, . Location in patent: Page/Page column 31-32
[4] Patent: WO2009/108838, 2009, A1, . Location in patent: Page/Page column 95-96
[5] Chemical Communications, 2013, vol. 49, # 39, p. 4304 - 4306
[6] Patent: US8822634, 2014, B2, . Location in patent: Page/Page column
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