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[ CAS No. 3336-16-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3336-16-1
Chemical Structure| 3336-16-1
Chemical Structure| 3336-16-1
Structure of 3336-16-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3336-16-1 ]

CAS No. :3336-16-1 MDL No. :MFCD00052185
Formula : C7H4ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :BDDVAWDNVWLHDQ-UHFFFAOYSA-N
M.W : 153.57 Pubchem ID :592797
Synonyms :

Calculated chemistry of [ 3336-16-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.19
TPSA : 44.02 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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.266 mg/ml ; 0.00173 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.158 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.477 mg/ml ; 0.0031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 3336-16-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3336-16-1 ]

* 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 [ 3336-16-1 ]
  • Downstream synthetic route of [ 3336-16-1 ]

[ 3336-16-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 3336-16-1 ]
  • [ 56962-11-9 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 20℃; for 19 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 0℃;
Diisobutylaluminium hydride (1M in hexane, 240 mL, 240 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (15 g, 97.7 mmol) in tetrahydrofuran (200 mL), cooled to -78° C., and the mixture was stirred at this temperature for 1 hour then at room temperature for 18 hours.
The mixture was then cooled to 0° C. and 1M hydrochloric acid (80 mL) was added dropwise.
The reaction mixture was diluted with water (200 mL) and filtered, washing through with ethyl acetate (*2).
The layers of the filtrate were separated and the organic solution was dried over magnesium sulfate and concentrated in vacuo.
Trituration of the residue with dichloromethane afforded the title compound as a solid in 84percent yield, 12.92 g.
Reference: [1] Patent: US2006/35922, 2006, A1, . Location in patent: Page/Page column 31
[2] Patent: WO2014/69963, 2014, A1, . Location in patent: Paragraph 885-886
[3] Patent: WO2007/136116, 2007, A2, . Location in patent: Page/Page column 83-85
  • 2
  • [ 20925-27-3 ]
  • [ 3336-16-1 ]
YieldReaction ConditionsOperation in experiment
62.5% With urea; sodium nitrite In sulfuric acid; water Step 5
A mixture of 2-chloro-4-aminobenzonitrile (25 g, 0.187 m) in stirred concentrated sulfuric acid (58 g) and water (570 ml) was heated at between 49° and 61° C. for approximately thirty minutes.
The suspension was cooled to approximately 0° C. and a cold solution of sodium nitrite (13.2 g, 0.187 m) in water (125 ml) was added dropwise at a solution temperature of between 0° and 6° C.
Stirring continued thereafter for approximately three hours and then urea (1.5 g) was added to the mixture.
The resulting insoluble impurity was filtered off.
An aqueous solution of 50percent sulfuric acid (600 ml) was added while the reaction mixture was heated at a temperature between 74° and 81° C. and stirred until the evolution of nitrogen gas ceased.
The reaction product was separated by filtration and then recrystallized from water to yield 2-chloro-4-hydroxybenzonitrile (17.9 g, 62.5percent, mp 160°
Reference: [1] Patent: US4424371, 1984, A,
  • 3
  • [ 7647-01-0 ]
  • [ 3336-16-1 ]
  • [ 56363-84-9 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 1, p. 67 - 72
  • 4
  • [ 3336-16-1 ]
  • [ 74-88-4 ]
  • [ 127666-99-3 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5 h;
Stage #2: at 20℃;
Example 12; 2-Amino-3-(3-chloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo [ 1 ,2-a] pyridin-2-yl)- 1 ,2,4- oxadiazol-3-yl)phenoxy)propanoic acid hydrochloride.; 2-Chloro-4-methoxy benzonitrile (63).; To a stirred solution of 2-chloro-4-hydroxy benzonitrile 62 (2.5 g, 16 mmol) in DMF (25 mL) was added NaH (0.431 g, 18.0 mmol) at 0 0C. After 30 min, methyl iodide (3.47 g, 24.4 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 1 h. After completion, the reaction mixture was quenched with ice water and extracted with diethyl ether. The organic layer was washed with water, saturated NaCl solution, dried over Na2SO4 and concentrated in vacuo to afford the title intermediate 63 as a brown solid (2.7 g, yield 98percent).
Reference: [1] Patent: WO2010/65760, 2010, A1, . Location in patent: Page/Page column 133-134
[2] Patent: WO2006/8046, 2006, A1, . Location in patent: Page/Page column 47
  • 5
  • [ 3336-16-1 ]
  • [ 104253-44-3 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 1, p. 67 - 72
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