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[ CAS No. 131674-39-0 ] {[proInfo.proName]}

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Chemical Structure| 131674-39-0
Chemical Structure| 131674-39-0
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Product Details of [ 131674-39-0 ]

CAS No. :131674-39-0 MDL No. :MFCD16037360
Formula : C7H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :FVMGQROBOUHKQO-UHFFFAOYSA-N
M.W : 157.60 Pubchem ID :14691917
Synonyms :

Calculated chemistry of [ 131674-39-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.18
TPSA : 33.12 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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 0.82
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.46 mg/ml ; 0.00927 mol/l
Class : Soluble
Log S (Ali) : -1.63
Solubility : 3.72 mg/ml ; 0.0236 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.512 mg/ml ; 0.00325 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 131674-39-0 ]

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 [ 131674-39-0 ]

* 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 [ 131674-39-0 ]
  • Downstream synthetic route of [ 131674-39-0 ]

[ 131674-39-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 131674-39-0 ]
  • [ 62838-65-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
  • 2
  • [ 131674-39-0 ]
  • [ 55676-21-6 ]
YieldReaction ConditionsOperation in experiment
81% With chromium(VI) oxide In acetone at -30 - 20℃; for 3 h; Step 2:
1-(2-Chloropyridin-3-yl)ethanone
A solution of 1-(2-chloropyridin-3-yl)ethanone (10 g, 0.0635 mol) in dry acetone (200 mL) was introduced under argon into a 1 L flask.
The mixture was cooled to -30° C. and pure, pulverized chromic anhydride (19 g, 0.19 mol) was added.
The reaction mixture was kept at room temperature for 3 h. 2-Propanol (100 mL) was added, followed by aqueous sodium hydrogen carbonate to pH 8.
After filtration, solids were washed with chloroform.
The organic and aqueous layers were then separated and the aqueous layer was extracted with chloroform (2*100 mL).
The combined organics were dried over anhydrous sodium sulfate and evaporated to yield the crude pyridyl ketone as an oil.
This product was purified by column chromatography (8 g, 81percent).
*1H NMR (CDCl3) 8.44 (dd, J=5 and 2 Hz, 1H) 7.91 (dd, J=7.5 and 2 Hz, 1H), 7.34 (dd, J=7.5 and 5 Hz, 1H), 2.68 (s, 3H).
81% With chromium(VI) oxide In acetone at -30 - 20℃; for 3 h; Inert atmosphere Step 2: l-(2-Chloropyridin-3-yl)ethanone.A solution of l-(2-chloropyridin-3-yl)ethanone (1O g, 0.0635 mol) in dry acetone (200 mL) was introduced under argon into a 1 L flask. The mixture was cooled to -30 0C and pure, pulverized chromic anhydride (19 g, 0.19 mol) was added. The reaction mixture was kept at room temperature for 3 h. 2-Propanol (100 mL) was added, followed by aqueous sodium hydrogen carbonate to pH 8. After filtration, solids were washed with chloroform. The organic and aqueous layers were then separated and the aqueous layer was extracted with chloroform (2x10OmL). The combined organics were dried over anhydrous sodium sulfate and evaporated to yield the crude pyridyl ketone as an oil. This product was purified by column chromatography (8 g, 81percent). *1H NMR (CDCl3) 8.44 (dd, J = 5 and 2 Hz, 1 H) 7.91 (dd, J = 7.5 and 2 Hz, 1 H), 7.34 (dd, J = 7.5 and 5 Hz, 1 H), 2.68 (s, 3 H).
77% With chromium(VI) oxide In acetone at -30 - 20℃; for 3.25 h; Inert atmosphere Step 2[00176] To a solution of l-(2-chloropyridin-3-yl)ethanol (II) in dry acetone at - 30°C under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol). The solution was further stirred 15 min at -30°C and allowed to warm to room temperature. The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL). The solution was made alkaline by slowly adding a saturated NaHC03 solution. The solution was filtered through a bed of Celite. The solids were washed by DCM. The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2 x 50 mL). The combined organic layers were dried over MgS04, filtered and concentrated under reduced pressure to yield l-(2-chloropyridin-3-yl)ethanone (III) as a brown liquid (0.72 g, 4.63 mmol, 77percent yield). 1H NMR (CDC13) δ ppm 2.71 (s, 3 H), 7.35 (dd, J=7.63, 4.80 Hz, 1 H), 7.91 (dd, J=7.54, 1.88 Hz, 1 H), 8.55 (dd, J=4.71, 1.88 Hz, 1 H).
77% With chromium(VI) oxide In acetone at -30 - 20℃; for 3.25 h; Inert atmosphere To a solution of 1-(2-chloropyridin-3-yl)ethanol (XII) in dry acetone at −30° C. under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol). The solution was further stirred 15 min at −30° C. and allowed to warm to room temperature. The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL). The solution was made alkaline by slowly adding a saturated aqueous NaHCO3 solution. The solution was filtered through a bed of Celite. The solids were washed by DCM. The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield 1-(2-chloropyridin-3-yl)ethanone (XIII) as a brown liquid (0.72 g, 4.63 mmol, 77percent yield). 1H NMR (CDCl3) δ ppm 2.71 (s, 3H), 7.35 (dd, J=7.63 Hz, J=4.80 Hz, 1H), 7.91 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.55 (dd, J=4.71 Hz, J=1.88 Hz, 1H).
77% With chromium(VI) oxide In acetone at -30 - 20℃; for 3.25 h; Inert atmosphere Step 2
To a solution of 1-(2-chloropyridin-3-yl)ethanol (X) in dry acetone at -30° C. under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol).
The solution was further stirred 15 min at -30° C. and allowed to warm to room temperature.
The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL).
The solution was made alkaline by slowly adding a saturated aqueous NaHCO3 solution.
The solution was filtered through a bed of Celite.
The solids were washed by DCM.
The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2*50 mL).
The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield 1-(2-chloropyridin-3-yl)ethanone (XI) as a brown liquid (0.72 g, 4.63 mmol, 77percent yield).
1H NMR (CDCl3) δ ppm 2.71 (s, 3H), 7.35 (dd, J=7.63 Hz, J=4.80 Hz, 1H), 7.91 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.55 (dd, J=4.71 Hz, J=1.88 Hz, 1H).
77% With chromium(VI) oxide In acetone at -30 - 20℃; for 3.25 h; To a solution of 1-(2-chloropyridin-3-yl)ethanol (X) in dry acetone at -30°C under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol). The solution was further stirred 15 min at -30°C and allowed to warm to room temperature. The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL). The solution was made alkaline by slowly adding a saturated aqueous NaHCCb solution. The solution was filtered through a bed of Celite. The solids were washed by DCM. The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2 x 50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield 1 -(2-chloropyridin-3 -yl)ethanone (XI) as a brown liquid (0.72 g, 4.63 mmol, 77percent yield). 1H NMR (CDCl3) δ ppm 2.71 (s, 3H), 7.35 (dd, J=7.63Hz, J=4.80Hz, 1H), 7.91 (dd, J=7.54Hz, J=1.88Hz, 1H), 8.55 (dd, J=4.71Hz, J=1.88Hz, 1H).

Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
[2] Patent: US2006/47126, 2006, A1, . Location in patent: Page/Page column 30
[3] Patent: WO2011/5759, 2011, A2, . Location in patent: Page/Page column 77
[4] Patent: WO2011/84486, 2011, A1, . Location in patent: Page/Page column 106; 110-111
[5] Patent: US2013/296302, 2013, A1, . Location in patent: Paragraph 0494
[6] Patent: US2016/68550, 2016, A1, . Location in patent: Paragraph 1056
[7] Patent: WO2016/40193, 2016, A1, . Location in patent: Paragraph 0703
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
  • 3
  • [ 131674-39-0 ]
  • [ 65326-33-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
  • 4
  • [ 131674-39-0 ]
  • [ 131674-40-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
  • 5
  • [ 131674-39-0 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 6
  • [ 131674-39-0 ]
  • [ 116855-08-4 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 7
  • [ 131674-39-0 ]
  • [ 916325-85-4 ]
Reference: [1] Patent: WO2011/84486, 2011, A1,
[2] Patent: US2013/296302, 2013, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 8
  • [ 131674-39-0 ]
  • [ 916325-83-2 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
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