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[ CAS No. 71590-31-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 71590-31-3
Chemical Structure| 71590-31-3
Structure of 71590-31-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 71590-31-3 ]

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Product Details of [ 71590-31-3 ]

CAS No. :71590-31-3 MDL No. :MFCD26743552
Formula : C10H9BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :PIUVTVGJKFGBJL-UHFFFAOYSA-N
M.W : 258.54 Pubchem ID :71607240
Synonyms :

Calculated chemistry of [ 71590-31-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.02
TPSA : 26.02 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) : -5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.77
Log Po/w (WLOGP) : 3.99
Log Po/w (MLOGP) : 3.52
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.39
Solubility : 0.0106 mg/ml ; 0.000041 mol/l
Class : Moderately soluble
Log S (Ali) : -4.01
Solubility : 0.0253 mg/ml ; 0.0000978 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00691 mg/ml ; 0.0000267 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 71590-31-3 ]

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 [ 71590-31-3 ]

* 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 [ 71590-31-3 ]
  • Downstream synthetic route of [ 71590-31-3 ]

[ 71590-31-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5773-80-8 ]
  • [ 71590-31-3 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With diphenyl phosphoryl azide; triethylamine In <i>tert</i>-butyl alcohol for 15 h; Reflux
Stage #2: With hydrogenchloride In methanol at -78 - 20℃; for 15 h;
A mixture of 6-bromo-2-naphthoic acid (80.3 g, 319 mmol), diphenylphosphoryL azide (71 mL, 352 mmol) and triethylamine (50 mL, 358 mmol) in fert-butanol (400 mL) was heated to reflux and allowed to stir at this temperature for 15 hours. The reaction mixture was then cooled to room temperature and poured over saturated aqueous NaHC03 solution (6Ψ0 mL) and stirred vigorouslyfor 30 minutes. The resulting suspension was filtered, washed with water (200 mL) and dried in vacuo at 65 °C. The resulting white solid was suspended in MeOH (500 mL) and cooled to -78 °C, then HCl gas was bubbled into the mixture until saturated. The reaction mixture was then allowed to stir at room -temperature for 15 hours, after which time the resulting solids were collected by filtration, then washed with- ice-cold MeOH (100 mL) to provide Compound Int-6a as an off-white solid (74.8 g, 91percent), which was used without further purification. l NM (DMSO-_3/4) 6 10.5-10.0 (br s, 3H), 8.23 (s, 1H), 7.99 (d, J= 9.0 Hz, 1H), 7.92 (d, J= 9.0 Hz, 1H), 7.84 (s, 1H), 7.68-7.65 (m, 1H), 7.56-7.51 (m, 1H . "LRMS: (M+2H)+ = 223.
91%
Stage #1: With diphenyl phosphoryl azide; triethylamine In <i>tert</i>-butyl alcohol for 15 h; Reflux
Stage #2: With sodium hydrogencarbonate In tert-butyl methyl ether for 0.5 h;
Stage #3: With hydrogenchloride In methanol at -78 - 20℃; for 15 h;
Preparation of Compound 1A1AA mixture of 6-bromo-2--naphthoic acid-(80.3 g, 319 mmol),diphenylphosphorylazide (71 mL, 352 mmol) and triethylamine (50 mL, 358 mmol) in fer/-butanol (400 mL) was heated to reflux for 15 hours then cooled to room temperature. The reaction mixture was poured over saturated NaHC03 (600 mL) and stirred vigorously for 30 minutes. The solids were filtered, washed with water (200 mL) and dried under vacuum at 65 °C. The resulting. white solid was suspended in MeOH (500 mL), then HCl(g) was bubbled into the mixture at -78 °C until saturated. The reaction mixture was stirred at room temperature for 15 hours, then the resulting solids were collected by filtration, and washed with ice-cold MeOH (100 mL) to provide Compound 1A as an off- white solid (74.8 g, 91percent). 1H NMR (DMSO-<4) δ 10.5-10.0 (br s, 3H), 8.23 (s, 1H), 7.99 (d, J= 9.0 Hz, 1H), 7.92 (d, J= 9.0 Hz, 1H), 7.84 (s, 1H), 7.68-7.65 (m, 1H), 7.56-7.51 (m, 1H). LRMS: (M+2H)+ = 223.
Reference: [1] Patent: WO2011/87740, 2011, A1, . Location in patent: Page/Page column 74
[2] Patent: WO2011/66241, 2011, A1, . Location in patent: Page/Page column 108
[3] Patent: EP2545060, 2015, B1, . Location in patent: Paragraph 0328; 0329
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