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[ CAS No. 3215-64-3 ]

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Chemical Structure| 3215-64-3
Chemical Structure| 3215-64-3
Structure of 3215-64-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3215-64-3 ]

CAS No. :3215-64-3 MDL No. :MFCD00001901
Formula : C8H5Cl2N Boiling Point : -
Linear Structure Formula :- InChI Key :AOEJUUCUKRUCEF-UHFFFAOYSA-N
M.W :186.04 Pubchem ID :76678
Synonyms :

Calculated chemistry of [ 3215-64-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.98
TPSA : 23.79 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) : -5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 3.06
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 2.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.212 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.365 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.12
Solubility : 0.0141 mg/ml ; 0.0000757 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 3215-64-3 ]

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 [ 3215-64-3 ]

* 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 [ 3215-64-3 ]
  • Downstream synthetic route of [ 3215-64-3 ]

[ 3215-64-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 151-50-8 ]
  • [ 2014-83-7 ]
  • [ 3215-64-3 ]
YieldReaction ConditionsOperation in experiment
95% With 18-crown-6 ether In ethanol; water for 1 - 3 h; Heating / reflux EXAMPLE 13-(2,6-DichIoro-phenyl)-6-(2,4-difluoro-phenyIamino)-l-niethyl-pyrazolo[l,5-a]pyrimidin-2-one:Step l(2,6-DichIorophenyI)-acetonitrile: A 500 mL round-bottom flask was charged with a solution of KCN (26 g, 400.00 mmol) ,18-crown-6 (0.05 g) in water (60 ml). To this was added 1 ,3-dichloro-2- (chloromethyl)benzene (40 g, 206.24 mmol) in ethanol (300 ml). The resulting solution was allowed to stir for 1~3 hours while the temperature was maintained at reflux. The reaction progress was monitored by TLC (AcOEt: PE=I :4). The mixture was the concentrated to dryness on a rotary evaporator. The resulting residue was the transferred into a seperatory funnel, washed with water (5 x 100 mL) to afford 35.4 g (95percent) of 2-(2,6-dichlorophenyl)acetonitrile as a white solid. This product was used without further purification.
Reference: [1] Patent: WO2007/15866, 2007, A2, . Location in patent: Page/Page column 29; 31
  • 2
  • [ 143-33-9 ]
  • [ 2014-83-7 ]
  • [ 3215-64-3 ]
Reference: [1] Chemische Berichte, 1975, vol. 108, p. 2448 - 2464
[2] Phytochemistry (Elsevier), 1988, vol. 27, # l, p. 51 - 72
  • 3
  • [ 5413-85-4 ]
  • [ 17518-49-9 ]
  • [ 3215-64-3 ]
  • [ 1160608-75-2 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 2, p. 382 - 388
  • 4
  • [ 882769-94-0 ]
  • [ 17518-49-9 ]
  • [ 3215-64-3 ]
  • [ 1160606-90-5 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 2, p. 382 - 388
  • 5
  • [ 3215-64-3 ]
  • [ 6575-24-2 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With potassium hydroxide; water In ethanol at 80℃; for 20 h;
Stage #2: With hydrogenchloride In ethanol
A solution of (2,6-dichloro-phenyl)-acetonitrile (Intermediate A1) (commercially available at Aldrich) (18.6 g, 100 mmol) in ethanol (40 mL) and water (50 mL) was treated with KOH (30 g) and the mixture was heated to 80° C. for 20 h. The mixture was quenched with HCl until pH 3. The product was extracted with chloroform (5.x.50 mL). The extracts were combined, dried over MgSO4, filtered and evaporated to dryness. The product was (2,6-dichloro-phenyl)-acetic acid, 17 g (83percent). A solution of (2,6-dichloro-phenyl)-acetic acid (10 g, 49 mmol) in benzene (200 mL) was treated with oxalyl chloride (32 mL, 2M in dichloromethane) followed by a few drops of dimethyl formamide. The mixture was allowed to stir for 3.5 h at rt. The solvent was removed under vacuum to give 11.5 g of (2,6-dichloro-phenyl)-acetyl chloride (Intermediate A2). The acid chloride, Intermediate A2 (6 g, 26.8 mmol) was added via pipette to a solution of diazomethane in ether (30 mmol) (generated from Diazald by standard Aldrich diazomethane kit) at 0° C. After 35 m, HBr (conc.) (10 mL) was added at 0° C. This was allowed to react for 35 m. The ether was removed and the mixture was neutralized with sodium bicarbonate solution. The organic layer was removed and dried over MgSO4. The mixture was filtered and concentrated under reduced pressure to give 1-bromo-3-(2,6-dichloro-phenyl)-propan-2-one (Intermediate A3) (5 g, 66percent). 1-Bromo-3-(2,6-dichloro-phenyl)-propan-2-one (Intermediate A3) (2.5 g) was heated in formamide for 2 h at 180° C. and 150° C. for 1 additional h. Water (50 mL) was added and the mixture was extracted with chloroform (4.x.50 mL). The solution was washed with brine (1.x.30 mL), dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel with 5percent NH3-MeOH: CH2Cl2 to give the product 5-(2,6-dichloro-benzyl)-1H-imidazole (Intermediate A4), 400 mg. A solution of 5-(2,6-dichloro-benzyl)-1H-imidazole (Intermediate A4) (0.34 g, 1.5 mmol) in THF (6 mL) and water (6 mL) was treated with NaHCO3 (1.2 g) at rt for 10 m. Phenyl chlorothionoformate (0.60 mL, 4.3 mmol) was added and stirring was continued for 3 h. The mixture was diluted with water (10 mL) and extracted with ether (4.x.15 mL). The organic portions were combined, dried over MgSO4, filtered and freed of solvent. The residue was dissolved in MeOH (6 mL) and treated with NEt3 (0.6 mL) for 18 h. The solvent was removed under vacuum and the product was washed on a glass frit with CH2Cl2 to give a white solid 4-(2,6-dichloro-benzyl)-1,3-dihydro-imidazole-2-thione (Compound 1) in 50percent yield. 1H NMR (300 MHz, DMSO-d6): δ 12.0 (s, 1H), 11.7 (s, 1H), 7.50 (d, J=5.1 Hz, 2H), 7.35 (t, J=6.0 Hz, 1H), 6.04 (s, 1H), 3.98 (s, 2H).
Reference: [1] Patent: US2006/69142, 2006, A1, . Location in patent: Page/Page column 9-10
[2] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 1012
[3] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 477 - 480
[4] Chemische Berichte, 1975, vol. 108, p. 2448 - 2464
[5] Phytochemistry (Elsevier), 1988, vol. 27, # l, p. 51 - 72
[6] Chemical Communications, 2015, vol. 51, # 13, p. 2660 - 2662
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