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[ CAS No. 55304-90-0 ] {[proInfo.proName]}

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Chemical Structure| 55304-90-0
Chemical Structure| 55304-90-0
Structure of 55304-90-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 55304-90-0 ]

CAS No. :55304-90-0 MDL No. :MFCD11036367
Formula : C6H5Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :FWEVVZQDRPWAND-UHFFFAOYSA-N
M.W : 178.02 Pubchem ID :12259932
Synonyms :

Calculated chemistry of [ 55304-90-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.38
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 1.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.547 mg/ml ; 0.00307 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.1 mg/ml ; 0.00619 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.146 mg/ml ; 0.000822 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 55304-90-0 ]

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

Application In Synthesis of [ 55304-90-0 ]

* 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 [ 55304-90-0 ]
  • Downstream synthetic route of [ 55304-90-0 ]

[ 55304-90-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 55304-90-0 ]
  • [ 55304-73-9 ]
YieldReaction ConditionsOperation in experiment
80% With Dess-Martin periodane In dichloromethane at 20 - 26℃; for 2 h; To a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CH2C12 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26°C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5percent aqueous Na2S203 and stirred for 30 min. The resulting mixture was extracted with CH2C12 (2x30 ml). The combined organic layers were washed with saturated Na2S203 solution (50 ml), brine (30 ml), dried over Na2S04 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80percent). 1H NMR (400MHz, CDC13): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).
66% With pyridinium chlorochromate In dichloromethane for 2 h; Dissolve (2,6-dichloropyridin-3-yl)-methanol (876 mg, 4.92 mmol) in dichloromethane (20.mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite.(R). and silica gel and concentrate to give 2,6-dichloropyridine-3-carbaldehyde (575 mg, 66percent): 1H NMR (400 MHz5 CDCl3) δ 10.39 (s, IH)5 8.18 (d, IH, J = 8.0 Hz)5 7.43 (d, IH, J = 8.0 Hz).
Reference: [1] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00409
[2] Journal of Organic Chemistry, 1982, vol. 47, # 14, p. 2800 - 2802
[3] Patent: WO2006/44454, 2006, A1, . Location in patent: Page/Page column 62
[4] Patent: US3974166, 1976, A,
  • 2
  • [ 38496-18-3 ]
  • [ 55304-90-0 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With borane-THF In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; potassium carbonate In tetrahydrofuran for 2 h;
Dissolve 2,6-dichloronicotinic acid (1000 mg, 5.21 mmol) in anhydrous tetrahydrofuran (5 niL). Cool to 0 0C. Add borane-tetrahydrofuran complex (7.82 mL5 7.82 mmol, 1.0 M in tetrahydrofuran) slowly. Stir the mixture at room temperature overnight. Add water (1 niL) and potassium carbonate, stir for 2 hours, filter and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 20:80 ethyl acetate:hexanes to give (2,6-dichloropyridin-3-yl)-methanol (876 mg, 94percent). 1H NMR (400 MHz5 MeOH-d4) δ 7.96 (d, IH, J = 8.0 Hz), 7.45 (d, IH, J = 8.0 Hz), 4.64 (s, 2H).
80% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃; for 10 h; To a solution of 2,6-dichloronicotinic acid (1 g, 5.2 mmol) in THF (10 mL) was added NaBH4 (591 mg, 15.6 mmol) at 0°C. The mixture was stirred for 30 min and then BF3.OEt2 (2.2g, 15.6 mmol) was added drop wise at 0°C. After addition was complete, the mixture was stirred at room temperature for 10 hr, until the reaction was completed. The reaction mixture was quenched by the addition of saturated NH4C1 solution (50 mL) and extracted with ethyl acetate (3x30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the desired product as a white solid which was used in next step without further purification. (820 mg, Yield 80percent).
Reference: [1] Patent: WO2006/44454, 2006, A1, . Location in patent: Page/Page column 62
[2] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00408
[3] Patent: WO2006/85212, 2006, A2, . Location in patent: Page/Page column 43
[4] Patent: US6573274, 2003, B1,
  • 3
  • [ 55304-73-9 ]
  • [ 55304-90-0 ]
YieldReaction ConditionsOperation in experiment
3.01 g at 20℃; for 0.5 h; [1037] NaBH4 (808 mg, 21.3 mmol) was added to a solution of 514-1 (3.10 g, 17.7 mmol) in MeOH (22 niL), which had been pre-cooled to 0 °C. The mixture was allowed to reach r.t. and stirring was prolonged for 30 mins. 1 M aq. HC1 solution was added, and the organic solvent was removed under reduced pressure. The aqueous phase was extracted with DCM (3x). The combined organic portions were dried with and filtered. The volatiles were removed under reduced pressure to afford 514-2 (3.01 g). UPLC/MS(ES+): m/z 178.00 [M+H]+.
Reference: [1] Organic Letters, 2011, vol. 13, # 3, p. 526 - 529
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
[3] Patent: WO2012/78608, 2012, A1, . Location in patent: Page/Page column 28
[4] Patent: WO2015/26792, 2015, A1, . Location in patent: Paragraph 1037
  • 4
  • [ 58584-83-1 ]
  • [ 55304-90-0 ]
Reference: [1] Patent: WO2007/21710, 2007, A1, . Location in patent: Page/Page column 73
  • 5
  • [ 55366-29-5 ]
  • [ 55304-90-0 ]
Reference: [1] Patent: US3974166, 1976, A,
  • 6
  • [ 58584-86-4 ]
  • [ 55304-90-0 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 14, p. 2800 - 2802
  • 7
  • [ 2402-78-0 ]
  • [ 55304-90-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
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