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[ CAS No. 128072-93-5 ] {[proInfo.proName]}

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Chemical Structure| 128072-93-5
Chemical Structure| 128072-93-5
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Product Details of [ 128072-93-5 ]

CAS No. :128072-93-5 MDL No. :MFCD07772018
Formula : C8H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BEBBWTPLBRZIOF-UHFFFAOYSA-N
M.W : 185.61 Pubchem ID :15414989
Synonyms :

Calculated chemistry of [ 128072-93-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.33
TPSA : 39.19 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) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.16
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.85
Solubility : 0.261 mg/ml ; 0.00141 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.13 mg/ml ; 0.000699 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.12
Solubility : 0.14 mg/ml ; 0.000753 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 128072-93-5 ]

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 [ 128072-93-5 ]

* 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 [ 128072-93-5 ]
  • Downstream synthetic route of [ 128072-93-5 ]

[ 128072-93-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 128072-93-5 ]
  • [ 119830-47-6 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 5, p. 414 - 418
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  • [ 16110-09-1 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 5552-44-3 ]
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Reference: [1] Heterocycles, 1999, vol. 51, # 11, p. 2589 - 2602
  • 3
  • [ 128072-93-5 ]
  • [ 31181-89-2 ]
YieldReaction ConditionsOperation in experiment
52% With diisobutylaluminium hydride In dichloromethane; toluene for 0.333333 h; 5-Chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 76. [3percent)] was obtained obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid (200 mg, 1.03 mmol) with ethanol (3 mL) and 4M [HC1] in dioxane (0.5 mL) at 90 [°C] for 20 h. 5-Chloro-pyridine-2-carbaldehyde (58 mg, 52percent) was obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 0.786 mmol) with 1 M DIBAL in toluene (1.74 mL, 1.74 mmol) in dichloromethane (4.0 mL) 20 min. GC-MS [(M+)] : 141
Reference: [1] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 42
  • 4
  • [ 128072-93-5 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With diisopropyl aluminium hydride In tetrahydrofuran; toluene at 0℃; for 2 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol; toluene at 0 - 20℃; for 3 h;
Stage #3: With methanol; water; sodium sulfate In tetrahydrofuran; diethyl ether; toluene at 20℃;
(1)
Production of (5-chloropyridin-2-yl)methanol:
With cooling with ice, a toluene solution (66 mL, 66.0 mmol) of 1 N diisopropylaluminium hydride was gradually added to a THF solution (40 mL) of ethyl 5-chloropyridine-2-carboxylate (4.05 g, 22.0 mmol) [Heterocycles, 51(11), 2589 (1999)], then stirred at 0°C for 2 hours.
Next, sodium borohydride (832 mg, 22.0 mmol) and methanol (10 mL) were added to the reaction liquid with cooling with ice, and stirred at room temperature for 3 hours.
Ether was added to the reaction liquid, then water (5 mL) and sodium sulfate 10-hydrate were added, and stirred overnight at room temperature.
The insoluble matter was removed from the reaction liquid by filtration through Celite, then the obtained filtrate was concentrated under reduced pressure to obtain the entitled compound (3.14 g, 100 percent).
1H-NMR (400 MHz, CDCl3, δ ppm): 4.75 (2H, s), 7.20-7.30 (1H, m), 7.67 (1H, dd, J=8.0, 2.4 Hz), 8.53 (1H, d, J=2.4 Hz).
74.6%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 20℃;
Ethyl S-chloro^-pyridinecarboxylate (104.0 mg, 0.560 mmol) was dissolved in THF (5.6 mL) and cooled to 00C. The reaction mixture was then slowly treated with lithium aluminum hydride l.OM solution in THF (0.392 μL, 0.392 mmol) and warmed to ambient temperature. The reaction mixture was allowed to stir at ambient temperature for 1 hour and then cooled to 00C. The reaction mixture was then treated with water (15 μL) followed by l.ON NaOH (15 μL) and then water (45 μL). The reaction mixture was warmed to ambient temperature and allowed to stir for 30 minutes. The reaction mixture was diluted with EtOAc, filtered through glass microfibre filter ("GF/F") paper and concentrated. Silica gel chromatography eluting with a gradient of 50percent hexanes/EtOAc to 100percent hexanes/EtOAc provided (5-chloropyridin-2-yl)methanol (60.0 mg, 0.418 mmol, 74.6percent yield).
Reference: [1] Patent: EP1916239, 2008, A1, . Location in patent: Page/Page column 28
[2] Patent: WO2011/25968, 2011, A1, . Location in patent: Page/Page column 41-42
[3] Patent: EP1748048, 2007, A1, . Location in patent: Page/Page column 34
  • 5
  • [ 86873-60-1 ]
  • [ 64-17-5 ]
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YieldReaction ConditionsOperation in experiment
84%
Stage #1: at 80℃; for 16 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
A mixture of 5-chloro-2-pyridinecarboxylic acid (1.0 g, 6.35 mmol) and cone. H2SO4 (0.1 ml) was heated in EtOH (10 ml) at 80 0C for 16 hours. After cooling and concentrating at reduced pressure, the residue was dissolved in EtOAc (50 ml), washed with saturated NaHCO3 (25 ml) and brine (25 ml), dried (MgSO4), filtered and re-concentrated at reduced pressure giving the title compound (990 mg, 84percent).LCMS data: Calculated MH+ (186); Found 98percent (MH+) m/z 186, Rt = 1.13 min. NMR data: 1H NMR (250 MHz, CDCl3) δ ppm 8.63 - 8.76 (1 H, m), 8.10 (1 H, d, J=8.4 Hz), 7.82 (1 H, dd, J=8.5, 2.4 Hz), 4.49 (2 H, q, J=7.2 Hz), 1.45 (3 H, t, J=7.2 Hz).
76.6% With hydrogenchloride In 1,4-dioxane at 90℃; for 20 h; 5-Chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 76. [3percent)] was obtained obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid (200 mg, 1.03 mmol) with ethanol (3 mL) and 4M [HC1] in dioxane (0.5 mL) at 90 [°C] for 20 h. 5-Chloro-pyridine-2-carbaldehyde (58 mg, 52percent) was obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 0.786 mmol) with 1 M DIBAL in toluene (1.74 mL, 1.74 mmol) in dichloromethane (4.0 mL) 20 min. GC-MS [(M+)] : 141
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3516 - 3540
[2] Patent: WO2009/135842, 2009, A1, . Location in patent: Page/Page column 76
[3] Chemistry - A European Journal, 2014, vol. 20, # 13, p. 3610 - 3615
[4] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 42
[5] Patent: US2011/237791, 2011, A1, . Location in patent: Page/Page column 66
  • 6
  • [ 40473-01-6 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
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Reference: [1] Patent: EP1748048, 2007, A1, . Location in patent: Page/Page column 33
[2] Patent: US2003/236270, 2003, A1, . Location in patent: Page 44
  • 7
  • [ 16110-09-1 ]
  • [ 75-36-5 ]
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Reference: [1] Patent: US2003/186969, 2003, A1,
  • 8
  • [ 16110-09-1 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 128072-93-5 ]
Reference: [1] Heterocycles, 1999, vol. 51, # 11, p. 2589 - 2602
[2] Tetrahedron Letters, 1999, vol. 40, # 19, p. 3719 - 3722
  • 9
  • [ 16110-09-1 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 5552-44-3 ]
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Reference: [1] Heterocycles, 1999, vol. 51, # 11, p. 2589 - 2602
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