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[ CAS No. 791595-74-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 791595-74-9
Chemical Structure| 791595-74-9
Chemical Structure| 791595-74-9
Structure of 791595-74-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 791595-74-9 ]

CAS No. :791595-74-9 MDL No. :MFCD06659788
Formula : C7H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :YLKNNXAMJFCCPY-UHFFFAOYSA-N
M.W : 212.05 Pubchem ID :20430861
Synonyms :

Calculated chemistry of [ 791595-74-9 ]

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 : 2.0
Molar Refractivity : 48.2
TPSA : 54.7 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 1.54
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.221 mg/ml ; 0.00104 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.411 mg/ml ; 0.00194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.0823 mg/ml ; 0.000388 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 791595-74-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P261-P301+P310-P305+P351+P338-P308+P313 UN#:2811
Hazard Statements:H301-H315-H319-H335-H361 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 791595-74-9 ]

* 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 [ 791595-74-9 ]
  • Downstream synthetic route of [ 791595-74-9 ]

[ 791595-74-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 506-68-3 ]
  • [ 1575-37-7 ]
  • [ 791595-74-9 ]
YieldReaction ConditionsOperation in experiment
94% at 50℃; for 1 h; O.
5-Bromo-2-aminobenzimidazole (11)
5-Bromo-2-aminobenzimidazole (11) was synthesized according to a modified version of a reported procedure. [31] In brief, 4-bromo-1,2-diaminobenzene (1.0 g, 5.35 mmol, 1.0 eq.) was dissolved in a 1:1 mixture of MeOH (40 mL) and water (40 mL) in a 250 mL round bottom flask.
The reaction mixture was treated with CNBr (1.7 g, 16.04 mmol, 3.0 eq.) and heated at 50° C. for 1 h.
After cooling to room temperature, the MeOH was removed in vacuo, and the remaining mixture was basified with 1.0 M aq. NaOH (to pH=8.0) and extracted with EtOAc (3*30 mL).
86% for 0.0833333 h; Step A5-bromo-N-(tert-butyl)- e-3-sulfonamide[00400] A deep brown solution of 4-bromo-1 ,2-benzenediamine (4 g, 21.39 mmol) in MeOH (20 mL) was treated with cyanic bromide (2.492 g, 23.52 mmol). The reaction was exothermic, and the methanol began to boil after a few seconds. After 5 minutes the reaction mixture was diluted with EtOAc (100 mL), washed with a sat. NaHC03 solution (100 mL) and a sat. NaCI solution (100 mL). The organic layer was concentrated to a few mL, loaded onto silica cartridge and purified by column chromatography (0-20percent MeOH/EtQAc) to obtain 5-bromo-1 H- benzimidazol-2-amine (3.9 g, 18.39 mmol, 86 percent yield) as a black solid: 1H NMR (400 MHz, DMSO-cfe) δ ppm 6.47 (br. s., 2 H) 6.94 - 7.00 (m, 1 H) 7.01 - 7.06 (m, 1 H) 7.23 (d, J=1.85 Hz, 1 H) 8.70 - 1 1.33 (m, 1 H); ES LC-MS m/z =212.2 (Br79, M+H)+, ES LC-MS m/z =214.2 (Br81, M+H).
53% at 0 - 20℃; for 14 h; EXAMPLE 157; Scheme for the synthesis of N4-(5-brorao-lH-benzimidazol-2-yl)-N5-(5-bromo-2- methylphenyl)-lH-imidazole-4,5-dicarboxamide; Synthesis of 5-bromo-lH-benzo[d]imidazol-2-amine; [00421] Cyanogen bromide was added to a solution of 4-bromo-l,2-phenyldiamine (1.87 g, 10 mmole, commercially available from Aldrich) in acetonitrile (10 mL) and water (2 ml) at 0 0C. The reaction mixture was allowed to warm to room temperature and stirred for 14 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate (50 ml) and shaken. The resulting solid was filtered off, washed with water and dried at reduced pressure to give 1.13 g of 5-bromo-lH- benzo[d]imidazol-2-amine (yield, 53percent) as a yellow solid. MS (EI): 213 (MH+).
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 21, p. 5226 - 5229
[2] Patent: US2013/136782, 2013, A1, . Location in patent: Paragraph 0216; 0217
[3] Patent: WO2012/174312, 2012, A2, . Location in patent: Page/Page column 283-284
[4] Patent: WO2008/42282, 2008, A2, . Location in patent: Page/Page column 219-220
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1943 - 1948
  • 2
  • [ 55305-43-6 ]
  • [ 1575-37-7 ]
  • [ 791595-74-9 ]
YieldReaction ConditionsOperation in experiment
60% With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 5 - 20℃; for 1 h; Green chemistry General procedure: To a solution of o-aminophenol (400 mg, 3.67 mmol) and NCTS (998 mg, 3.67 mmol) in THF (6 mL), 1 M LiHMDS in hexane (3.67 mL, 3.67 mmol) was added and stirred at 5 °C to r.t. for 1h. Then the reaction mixture was poured in ice water and stirred for 15 min. Then extracted with EtOAc, the organic layer was separated. The organic layer was washed with brine solution.Then organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtained pure 2-aminobenzaxozole in 90percent yield (471 mg).
Reference: [1] Synlett, 2015, vol. 26, # 7, p. 897 - 900
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