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Chemical Structure| 38180-46-0
Chemical Structure| 38180-46-0
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Product Details of [ 38180-46-0 ]

CAS No. :38180-46-0 MDL No. :MFCD03788834
Formula : C6H3ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :YDPLFBIGFQFIDB-UHFFFAOYSA-N
M.W : 138.55 Pubchem ID :818258
Synonyms :

Calculated chemistry of [ 38180-46-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.96
TPSA : 36.68 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) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.4
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 0.967 mg/ml ; 0.00698 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.71 mg/ml ; 0.0123 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.278 mg/ml ; 0.002 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 38180-46-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 38180-46-0 ]

* 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 [ 38180-46-0 ]
  • Downstream synthetic route of [ 38180-46-0 ]

[ 38180-46-0 ] Synthesis Path-Upstream   1~33

  • 1
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 2
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Heterocycles, 1984, vol. 22, # 1, p. 93 - 96
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Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 4
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  • [ 67-66-3 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 6
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  • [ 57266-69-0 ]
Reference: [1] Patent: US4853027, 1989, A,
[2] Patent: CN105218437, 2016, A, . Location in patent: Paragraph 0007
  • 7
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  • [ 114080-95-4 ]
Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1987, vol. 27, # 9, p. 337 - 338
  • 8
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YieldReaction ConditionsOperation in experiment
98% With triethylamine In acetonitrile for 20 h; Heating / reflux S-Chloro-pyridine^-carbonitrile (145-C).; To a solution of compound 145-B, (22.37 g, 172.7 mmol) in acetonitrile (175 mL) was added triethylamine (48 mL, 346 mmol) and TMS-CN (56 mL, 420 mmol). The solution was heated at reflux for 20 h then evaporated in vacuo. The residue was partitioned between EtOAc (250 mL), 10percent aqueous Na2CO3 (50 mL), and filtered over celite. The organic portion of the filtrate was washed with 10percent aqueous Na2CO3 (2X50 mL), brine (50 mL), and the organics dried over Na2SO4, filtered, and evaporated in vacuo to afford a dark crystalline residue, which was dissolved in warm diethyl ether (200 mL), filtered, and evaporated in vacuo to afford compound 145-C as a tan-orange powder (23.41 g, 98percent). 1H-NMR (DMSO-rfβ): δ 7.78-7.84 (m, IH), 8.30 (d, IH), 8.73 (d, IH); MS: m/z 139.1 (MH+).
98% With triethylamine In acetonitrile for 20 h; Reflux 3-chloro-pyridine-2-carbonitrile (145-C).
To a solution of compound 145-B, (22.37 g, 172.7 mmol) in acetonitrile (175 mL) was added triethylamine (48 mL, 346 mmol) and TMS-CN (56 mL, 420 mmol).
The solution was heated at reflux for 20 h then evaporated in vacuo.
The residue was partitioned between EtOAc (250 mL), 10percent aqueous Na2CO3 (50 mL), and filtered over celite.
The organic portion of the filtrate was washed with 10percent aqueous Na2CO3 (2*50 mL), brine (50 mL), and the organics dried over Na2SO4, filtered, and evaporated in vacuo to afford a dark crystalline residue, which was dissolved in warm diethyl ether (200 mL), filtered, and evaporated in vacuo to afford compound 145-C as a tan-orange powder (23.41 g, 98percent).
1H-NMR (DMSO-d6): δ 7.78-7.84 (m, 1H), 8.30 (d, 1H), 8.73 (d, 1H); MS: m/z 139.1 (MH+).
Reference: [1] Patent: WO2009/12430, 2009, A1, . Location in patent: Page/Page column 215-216
[2] Patent: US2012/190674, 2012, A1, . Location in patent: Page/Page column 89
[3] Patent: US2004/77605, 2004, A1,
[4] Patent: WO2006/91858, 2006, A1, . Location in patent: Page/Page column 155
  • 9
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YieldReaction ConditionsOperation in experiment
50% With phosphorus pentachloride In toluene at 20 - 120℃; for 10 h; Inert atmosphere Example 4: At room temperature, 2-cyano-3-hydroxypyridine 0.46 g was added to a three-necked flask. Under a nitrogen atmosphere, 3.0 ml of toluene and 1.31 g of phosphorus pentachloride were added at a bath temperature of 120 ° C for 10 hours. The mixture was allowed to cool to 70 ° C and water was added to the solution and the aqueous layer was extracted with toluene. The organic layer thus obtained was washed with saturated aqueous sodium hydrogencarbonate solution and concentrated under reduced pressure to obtain 8.28 g of a solution containing 0.27 g of 2-cyano-3-chloropyridine. The yield of 2-cyano-3-chloropyridine was 50percent based on 2-cyano-3-hydroxypyridine.
Reference: [1] Patent: TW2016/510, 2016, A, . Location in patent: Page/Page column 15
  • 10
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YieldReaction ConditionsOperation in experiment
67% With triethylamine In diethyl ether; acetonitrile 44B.
3-Chloro-2-cyanopyridine
Compound 44A (2.59 g, 20 mmol), trimethylsilylcyanide (5.95 g, 60 mmol), Et3N (4.05 g, 40 mmol), and acetonitrile (20 mL) were combined in a 3-necked 250-mL round-bottomed flask under nitrogen and refluxed for 6 h, at which time HPLC analysis indicated complete consumption of starting material.
The cooled reaction mixture was concentrated under reduced pressure to give a brown semi-solid which was partitioned between 3 N aqueous Na2CO3 and CH2Cl2.
The organic layer was washed with water, brine, dried (MgSO4), filtered, and concentrated under reduced pressure.
The residue was purified by flash chromatography using 5percent Et2O/CH2Cl2 as eluent to give the product 44B as a white crystalline solid (1.84 g, 67percent).
1H NMR (CDCl3) 7.37 (dd, J=4.7, 8.4 Hz, 1H), 7.73 (dd, J=1.4, 8.2 Hz, 1H), 8.47 (dd, J=1.3, 4.6 Hz, 1H); LC/MS m/z 139 [M+H]+.
67% With triethylamine In diethyl ether; acetonitrile 44B.
3-Chloro-2-cyanopyridine
Compound 44A (2.59 g, 20 mmol), trimethylsilylcyanide (5.95 g, 60 mmol), Et3N (4.05 g, 40 mmol), and acetonitrile (20 mL) were combined in a 3-necked 250-mL round-bottomed flask under nitrogen and refluxed for 6 h, at which time HPLC analysis indicated complete consumption of starting material.
The cooled reaction mixture was concentrated under reduced pressure to give a brown semi-solid which was partitioned between 3 N aqueous Na2CO3 and CH2Cl2.
The organic layer was washed with water, brine, dried (MgSO4), filtered, and concentrated under reduced pressure.
The residue was purified by flash chromatography using 5percent Et2O/CH2Cl2 as eluent to give the product 44B as a white crystalline solid (1.84 g, 67percent).
1H NMR (CDCl3) 7.37 (dd, J=4.7, 8.4 Hz, 1 H), 7.73 (dd, J=1.4, 8.2 Hz, 1 H), 8.47 (dd, J=1.3, 4.6 Hz, 1 H); LC/MS m/z 139 [M+H]+.
Reference: [1] Patent: US2004/19063, 2004, A1,
[2] Patent: US2004/181064, 2004, A1,
  • 11
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Reference: [1] Patent: US5593986, 1997, A,
[2] Patent: US5604218, 1997, A,
[3] Patent: US5607926, 1997, A,
[4] Patent: US5756493, 1998, A,
[5] Patent: US5698547, 1997, A,
[6] Patent: US5789584, 1998, A,
  • 12
  • [ 100-70-9 ]
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Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 1, p. 135 - 137
[2] Tetrahedron, 2006, vol. 62, # 25, p. 5862 - 5867
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 22, p. 6442 - 6446[4] Angew. Chem., 2015, vol. 127, # 22, p. 6542 - 6546,5
  • 13
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YieldReaction ConditionsOperation in experiment
9.08 g With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 100℃; for 2 h; Production Example 13 (1) [0728] A mixture of 29.6 g of 2,3-dichloropyridine, 46.97 g of zinc cyanide, 11.56 g of tetratris(triphenylphosphine)palladium(0) and 150 mL of NMP was stirred at 100°C for 2 hours. Water was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 9.08 g of 3-chloropyridine-2-carbonitrile. 3-Chloropyridine-2-carbonitrile 1H-NMR (CDCl3) δ: 8.63 (1H, dd), 7.88 (1H, dd), 7.50 (1H, ddd)
Reference: [1] Patent: EP2881386, 2015, A1, . Location in patent: Paragraph 0728
  • 14
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Reference: [1] Patent: CN105218437, 2016, A, . Location in patent: Paragraph 0007
  • 15
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Reference: [1] Patent: US4853027, 1989, A,
  • 16
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4611 - 4616
[2] Patent: US2003/55085, 2003, A1,
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  • [ 1851-22-5 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Heterocycles, 1984, vol. 22, # 1, p. 93 - 96
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Reference: [1] Synthesis, 2005, # 6, p. 993 - 997
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Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 20
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  • [ 38180-46-0 ]
Reference: [1] Patent: US2012/190674, 2012, A1,
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  • [ 38180-46-0 ]
Reference: [1] Patent: CN105218437, 2016, A,
  • 22
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  • [ 38180-46-0 ]
Reference: [1] Patent: TW2016/510, 2016, A,
  • 23
  • [ 4513-94-4 ]
  • [ 67-66-3 ]
  • [ 89809-64-3 ]
  • [ 38180-46-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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  • [ 616-47-7 ]
  • [ 67-66-3 ]
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  • [ 17180-94-8 ]
  • [ 51269-82-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
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Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
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YieldReaction ConditionsOperation in experiment
88% at 4 - 25℃; for 2 h; Inert atmosphere Sodium methoxide (0.41 g, 7.5 mmol) was dissolved in 10 mL anhydrous N,N-dimethylformamide in a 25 mL round bottom flask under a nitrogen atmosphere and cooled to 4 °C with an ice water bath. 3-Chloro-2-cyanopyridine (1.01 g, 7.2 mmol) was added, the ice water bath was removed, and the reaction was warmed to 25 °C . After 2 hours, the reaction was concentrated under vacuum and ethyl acetate was added to the residue and the mixture was filtered to remove the precipitate. The resulting filtrate was then concentrated on a rotary evaporator to obtain the desired product as a white solid that was used without further purification (0.88g, 88percent yield). 1H-NMR(CDCl3) δ 8.22 (dd, J = 7.4 and 1.6Hz, 1H), 7.90 (dd, J = 7.5 and 7.3 Hz, 1H), 7.73 (dd, J = 7.73 and 1.6 Hz, 1H),3.92 (s, 3H). (ESI+): m/z (M+H)+ = 135.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359
[2] Patent: WO2015/187934, 2015, A1, . Location in patent: Paragraph 0205
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Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1990, vol. 30, # 7, p. 245 - 246
[2] Patent: WO2004/55003, 2004, A1, . Location in patent: Page 68
[3] Patent: WO2005/23807, 2005, A2, . Location in patent: Page/Page column 57
[4] Patent: US2005/215575, 2005, A1, . Location in patent: Page/Page column 19
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YieldReaction ConditionsOperation in experiment
58 g
Stage #1: for 2 h; Cooling with ice
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.5 h; Cooling with ice
In a mixture of 54 g of 3-chloropyridine-2-carbonitrile and 300 mL of THF, 500 g of 1 M methylmagnesium bromide THF solution was added dropwise under ice cooling. The reaction mixture was stirred for 2 hours under ice cooling. The reaction mixture obtained was added to 2N hydrochloric acid under ice cooling, and the mixture was stirred for 30 minutes. A 1N sodium hydroxide aqueous solution was added to the mixture, and the mixture was adjusted to pH 8, followed by extraction with ethyl acetate. After washing the organic layer with saturated brine, the organic layer was dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 58 g of an intermediate (12-1)
58 g
Stage #1: for 2 h; Cooling with ice
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.5 h; Cooling with ice
Preparation Example 2(1) (0639) To 3-chloropyridine-2-carbonitrile 54 g, and THF 300 mL, 1M THF solution of methyl magnesium bromide 500 mg was added dropwise under ice-cooling. The obtained reaction mixtures were stirred under ice-cooling for 2 hours. The obtained reaction mixtures were added to 2N hydrochloric acid under ice-cooling, and stirred for 30 minutes. To the mixtures was added 1N sodium hydroxide solution to adjust to pH 8, and the mixtures were extracted with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate. The organic layer was concentrated to give the Intermediate compound (4-1) 58 g. 1H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
58 g
Stage #1: for 2 h; Cooling with ice
Stage #2: With hydrogenchloride In tetrahydrofuran; water for 0.5 h; Cooling with ice
Preparation Example 12(1) To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL was added dropwise 1M methylmagnesium bromide solution in THF 500 g under ice-cooling. The reaction mixtures were stirred under ice-cooling for 2 hours. To 2N hydrochloric acid was added the resulting reaction mixtures under ice-cooling, and the mixtures were stirred for 30 minutes. The mixtures were made pH 8 with a 1N aqueous sodium hydroxide solution, and then the mixtures were extracted with ethyl acetate. The organic layers were washed with saturated brine, and then the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give an intermediate compound (12-1) 58 g.1H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
Reference: [1] Patent: JP2017/36339, 2017, A, . Location in patent: Paragraph 0178
[2] Patent: US2017/295787, 2017, A1, . Location in patent: Paragraph 0639
[3] Patent: US2017/305896, 2017, A1, . Location in patent: Paragraph 0621
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Reference: [1] Patent: US6387911, 2002, B1,
  • 30
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YieldReaction ConditionsOperation in experiment
50% With potassium fluoride In 1-methyl-pyrrolidin-2-one A solution of 2-cyano-3-chloropyridine (1 g, 7.22 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was treated with potassium fluoride (1.26 g, 21.68 mmol) and heated at reflux for 18 hours.
After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine.
Silica gel chromatography afforded 442 mg (50percent) of 2-cyano-3-fluoropyridine.
Reference: [1] Patent: US2003/55085, 2003, A1,
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  • [ 114080-93-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7357 - 7362
  • 32
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  • [ 488713-30-0 ]
Reference: [1] Patent: US2004/77605, 2004, A1,
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  • [ 379227-03-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359
[2] Patent: WO2015/187934, 2015, A1,
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