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[ CAS No. 635712-49-1 ] {[proInfo.proName]}

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Chemical Structure| 635712-49-1
Chemical Structure| 635712-49-1
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Product Details of [ 635712-49-1 ]

CAS No. :635712-49-1 MDL No. :MFCD11044594
Formula : C9H9BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :UXSIDFXINVIZIM-UHFFFAOYSA-N
M.W : 225.09 Pubchem ID :21102195
Synonyms :

Calculated chemistry of [ 635712-49-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.57
TPSA : 28.68 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) : -5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 2.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.64
Solubility : 0.0516 mg/ml ; 0.000229 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.111 mg/ml ; 0.000492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.56
Solubility : 0.00617 mg/ml ; 0.0000274 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 635712-49-1 ]

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 [ 635712-49-1 ]

* 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 [ 635712-49-1 ]
  • Downstream synthetic route of [ 635712-49-1 ]

[ 635712-49-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 70598-49-1 ]
  • [ 635712-49-1 ]
YieldReaction ConditionsOperation in experiment
79.2%
Stage #1: With potassium acetate; acetic anhydride In chloroform at 0 - 20℃; for 1 h; Inert atmosphere
Stage #2: With tert.-butylnitrite In chloroform at 60℃;
To a solution of 47-S2 (6 g, 28.2 mmol)and KOAc (3.3 g 33.8 mmol) in CHC13 (60 mL) was added dropwise acetic anhydride (8.6 g, 86.4mmol) at 0 DC under an atmosphere of nitrogen and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was heated to 60 CC and tert-butyl nitrite (5.8 g, 56.4 mmol) was added. The resulting mixture was stirred at 60 °C overnight. The mixture was diluted with DCM and washed with water and brine. The organic layer was dried over anhydrous Na2SO4and concentrated. The remaining residue was dissolved in MeOH and 6 N aqueous HC1 (20 mL) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was basified with 2 N aqueous NaOH solution and extracted with DCM twice. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford 47-S3 (5.0 g, 79.2percent yield) as a light a yellow solid. LC/MS (ESI) m/z: 225 (M+H) .
Reference: [1] Patent: WO2018/160889, 2018, A1, . Location in patent: Page/Page column 511; 512
  • 2
  • [ 943145-76-4 ]
  • [ 635712-49-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide for 1 h; Nitrogen atmosphere
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide
To a stirred solution of potassium t-butoxide (33.6 g, 10 equiv. ) in DMSO (200 mL) was added a solution of 4-bromo-2-ethyl-6-methylphenyldiazo-t-butyl sulfide (9. [4] g, 30 mmol) in DMSO (100 mL) via cannula. The mixture was stirred vigorously for 1 h. The reaction mixture was then carefully poured into a mixture of crushed ice (500 mL), concentrated hydrochloric acid (25 mL), and water (100 mL). The resulting precipitate was filtered, washed with water, dissolved in methanol, and concentrated to give 5.7 g (85percent) as a tan [SOLID. 1H-NMR (CDC13,] 500 MHz) [8 1.] 39 (t, J=7.6, 3H), 2.92 (q, [J=7.] 6,2H), 7.30 (s, 1H), 7.75 (s, 1H), 8.04 (s, 1H). Mass spec.: 225.00 [(MH) +.]
Reference: [1] Patent: WO2003/104236, 2003, A1, . Location in patent: Page 127
  • 3
  • [ 70598-49-1 ]
  • [ 635712-49-1 ]
  • [ 1031417-71-6 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With sodium nitrite In acetic acid at 20℃;
Stage #2: With sodium nitrite In water; acetic acid
To a solution of 2-ethyl-6-methylaniline (2.03 g, 15 mmol) in DMF (50 mL) at 0 C was added N-bromosuccinimide (2.66 g, 14.9 mmol). The mixture was stirred at room temperature for 10 minutes before addition to saturated aqueous NaCI. The mixture was extracted with EtOAc, the organic phase was washed with sat aqueous NaCI (2x), concentrated and the crude material was purified by Biotage chromatography (4OM, 15percent EtOAc/heptane) to provide 4-bromo-2-ethyl-6-methylbenzenamine as a red brown liquid (3.21 g, 100percent).A solution of 4-bromo-2-ethyl-6-methylbenzenamine (3.21 g, 15 mmol) in acetic acid (50 mL) was stirred for 3 hours before addition of a 2 M solution of sodium nitrite (11 mL, 22.5 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated and the solid was dissolved in EtOAc and washed with saturated aqueous NaCI (3x). The organic extract was dried over Na2SO4, filtered and concentrated, the crude material was purified by Biotage chromatography (4OM, 15- 30percent EtOAc/heptane) to provide 5-bromo-7-ethyl-1H-indazole (1.11 g, 33percent) and 5-bromo-3,7-dimethyl- 1H-indazole (0.84 g, 25percent).To a solution of 5-bromo-7-ethyl-1H-indazole (225 mg, 1.00 mmol) in dioxane (1.5 mL), hexacarbonylmolybdenum (132 mg, 0.50 mmol), Herrmann's catalyst (trans-Bis(acetato)bis[o-(di-o- tolylphosphino)benzyl]dipalladium) (46.9 mg, 0.05 mmol) and a solution of sodium carbonate (318 mg, 3.00 mmol) in water (2 mL). The suspension was sealed and irradiated in a microwave at 165 0C for 15 minutes (high absorption setting). The vial was vented , filtered through diatomaceous earth, washed with EtOAc and concentrated to provide the title compound (140 mg, 74percent).
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 935 - 942
[2] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 31
  • 4
  • [ 24549-06-2 ]
  • [ 635712-49-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 935 - 942
[2] Patent: WO2018/160889, 2018, A1,
[3] Patent: WO2008/65508, 2008, A1,
  • 5
  • [ 70598-49-1 ]
  • [ 635712-49-1 ]
  • [ 1031417-71-6 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With sodium nitrite In acetic acid at 20℃;
Stage #2: With sodium nitrite In water; acetic acid
To a solution of 2-ethyl-6-methylaniline (2.03 g, 15 mmol) in DMF (50 mL) at 0 C was added N-bromosuccinimide (2.66 g, 14.9 mmol). The mixture was stirred at room temperature for 10 minutes before addition to saturated aqueous NaCI. The mixture was extracted with EtOAc, the organic phase was washed with sat aqueous NaCI (2x), concentrated and the crude material was purified by Biotage chromatography (4OM, 15percent EtOAc/heptane) to provide 4-bromo-2-ethyl-6-methylbenzenamine as a red brown liquid (3.21 g, 100percent).A solution of 4-bromo-2-ethyl-6-methylbenzenamine (3.21 g, 15 mmol) in acetic acid (50 mL) was stirred for 3 hours before addition of a 2 M solution of sodium nitrite (11 mL, 22.5 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated and the solid was dissolved in EtOAc and washed with saturated aqueous NaCI (3x). The organic extract was dried over Na2SO4, filtered and concentrated, the crude material was purified by Biotage chromatography (4OM, 15- 30percent EtOAc/heptane) to provide 5-bromo-7-ethyl-1H-indazole (1.11 g, 33percent) and 5-bromo-3,7-dimethyl- 1H-indazole (0.84 g, 25percent).To a solution of 5-bromo-7-ethyl-1H-indazole (225 mg, 1.00 mmol) in dioxane (1.5 mL), hexacarbonylmolybdenum (132 mg, 0.50 mmol), Herrmann's catalyst (trans-Bis(acetato)bis[o-(di-o- tolylphosphino)benzyl]dipalladium) (46.9 mg, 0.05 mmol) and a solution of sodium carbonate (318 mg, 3.00 mmol) in water (2 mL). The suspension was sealed and irradiated in a microwave at 165 0C for 15 minutes (high absorption setting). The vial was vented , filtered through diatomaceous earth, washed with EtOAc and concentrated to provide the title compound (140 mg, 74percent).
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 935 - 942
[2] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 31
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