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[ CAS No. 89809-64-3 ] {[proInfo.proName]}

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Chemical Structure| 89809-64-3
Chemical Structure| 89809-64-3
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Product Details of [ 89809-64-3 ]

CAS No. :89809-64-3 MDL No. :MFCD03788835
Formula : C6H3ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :WTHODOKFSYPTKA-UHFFFAOYSA-N
M.W : 138.55 Pubchem ID :3833942
Synonyms :

Calculated chemistry of [ 89809-64-3 ]

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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.49
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) : -2.13
Solubility : 1.02 mg/ml ; 0.00739 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 1.88 mg/ml ; 0.0136 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 : 1.77

Safety of [ 89809-64-3 ]

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 [ 89809-64-3 ]

* 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 [ 89809-64-3 ]
  • Downstream synthetic route of [ 89809-64-3 ]

[ 89809-64-3 ] Synthesis Path-Upstream   1~24

  • 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
  • [ 16110-09-1 ]
  • [ 557-21-1 ]
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YieldReaction ConditionsOperation in experiment
59% at 160 - 185℃; Preparation 83; 5-Chloro-2-cvanopyridine ;Add in a 22-L 3-neck round bottom equipped with overhead stirrer, reflux condenser, and thermometer, N, N/-dimethylacetamide (DMAC, 6 L), 2,5- dichloropyridine (347.0 g, 2.34 mol), zinc cyanide (138.0 g, 1.17 mol), bis (diphenylphosphino) dipalladium II CH2Cl2 complex (DPPF, 20.8 g, 0.02 mol), and zinc dust (1.6 g, 0.02 mol). Slowly warm the reaction mixture to 160 ° C. As the temperature reaches 160 ° C, an exotherm (controllable) may result and the internal temperature may rise to 180-185 ° C. Remove the heat from the dark solution and cool the mixture slowly cool to room temperature. Extract the bulk reaction mixture by taking 2 L of the dark solution, diluting with brine (2L), filtering over celite, and addition of ethyl acetate (4L). Repeat the process 3 times to extract all material, and dry the combined organics over magnesium sulfate. Cautious concentration at 25-30 ° C might give a dark liquid. (Note: Product volatility maybe observed at higher temperatures so the temperature upon concentration is kept low in all steps. ) Stir the liquid and add water (5L), resulting in a solid After 1 h, filter, and back-wash with water (2L). Dry the filter cake to give 215 g of crude product. Extract the aqueous filtrate with ethyl ether (8L). Dry the organics over magnesium sulfate and concentrate to provide 51 g of crude product. Combine with the 215 g lot and purify by chromatography over silica gel (biotage 150; eluting with 5percent ethyl acetate in hexanes increasing to 10percent ethyl acetate in hexanes) to provide a white solid of pure title compound (193 g, 59percent) ; 1H NMR (CDCl3) 8 8.68 (d, J= 2.0 Hz, 1H), 7.84 (dd, J= 2.7, 8.6 Hz, 1H), 7.66 (d, J= 8.3 Hz, 1H).
Reference: [1] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 74-75
  • 3
  • [ 40473-01-6 ]
  • [ 89809-64-3 ]
Reference: [1] Patent: WO2010/132615, 2010, A1, . Location in patent: Page/Page column 131-132
  • 4
  • [ 544-92-3 ]
  • [ 244221-57-6 ]
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 16, p. 5215 - 5223
  • 5
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 16, p. 5215 - 5223
[2] Patent: US2003/55085, 2003, A1,
  • 6
  • [ 1851-22-5 ]
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  • [ 38180-46-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Heterocycles, 1984, vol. 22, # 1, p. 93 - 96
  • 7
  • [ 244221-57-6 ]
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Reference: [1] Patent: US2003/45546, 2003, A1,
  • 8
  • [ 626-60-8 ]
  • [ 7677-24-9 ]
  • [ 89809-64-3 ]
  • [ 38180-46-0 ]
  • [ 68325-15-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 9
  • [ 4513-94-4 ]
  • [ 67-66-3 ]
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  • [ 38180-46-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 10
  • [ 616-47-7 ]
  • [ 67-66-3 ]
  • [ 14508-49-7 ]
  • [ 17180-94-8 ]
  • [ 89809-64-3 ]
  • [ 51269-82-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 11
  • [ 460-19-5 ]
  • [ 126-99-8 ]
  • [ 89809-64-3 ]
  • [ 19235-89-3 ]
Reference: [1] Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 284
[2] Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 284
[3] Patent: US2494204, 1946, ,
[4] Patent: US2494204, 1946, ,
[5] Patent: US2494204, 1946, ,
  • 12
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  • [ 126-99-8 ]
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  • [ 19235-89-3 ]
Reference: [1] Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 284
[2] Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 284
[3] Patent: US2494204, 1946, ,
[4] Patent: US2494204, 1946, ,
[5] Patent: US2494204, 1946, ,
  • 13
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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
  • 14
  • [ 89809-64-3 ]
  • [ 86873-60-1 ]
YieldReaction ConditionsOperation in experiment
81.4% With water; sodium hydroxide In ethanol at 90 - 100℃; for 1.5 h; 1000ml four-necked flask, fitted with a stirrer, thermometer, reflux condenser, is added 5-chloro-2-cyano-pyridine (27.7g, 0.2mo), 277 mg of the ethanol, and dissolved with stirring, an aqueous solution of 10percent NaOH was added 277ml, heated to 90 ~ 100 stirred at reflux for 1.5h, TLC TLC [discriminating the end of reaction conditions to expand (butanol - acetic acid - water = 5: 2: 2)], the reaction is complete, cooled to room temperature under stirring, the pH was adjusted to 2 with 2NHCl ~ 3, and concentrated under reduced pressure to a volume of 100ml, methanol was added to 200ml, cooled to 0 ~ 5 , filtered, the solid out, and the filtrate was concentrated to dryness under reduced pressure, the residue was added 450ml of dichloromethane and 50ml of methanol, stirred for 1h, filtered and the solid with the amount of 10percent methanol - methylene chloride mixture was washed, 60 ~ 65 vacuum oven vacuum drying 2h, as a white solid intermediate 525.5g, a yield of 81.4percent.
Reference: [1] Patent: CN105348187, 2016, A, . Location in patent: Paragraph 0014; 0032
[2] Patent: WO2010/132615, 2010, A1, . Location in patent: Page/Page column 132
  • 15
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  • [ 132308-19-1 ]
Reference: [1] Patent: US2007/4772, 2007, A1, . Location in patent: Page/Page column 83
  • 16
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  • [ 132308-19-1 ]
Reference: [1] Patent: US2006/287341, 2006, A1, . Location in patent: Page/Page column 47
  • 17
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  • [ 67938-76-5 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride; hydrogen In ethanol; water for 2 h; A solution of 5-chloropicolinonitrile (3.8 g, 27.43 mmol), conc. HCl (3 mL) and 10percent Pd-C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2 h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4x25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51percent yield). LCMS (M+H) calcd for C6H8ClN2: 143.04; found: 143.07. 1HNMR (500 MHz, CDCl3) ? ppm: 8.56-8.51 (1H, br d), 7.66-7.60 (1H, m), 7.28-7.14 (1H, m), 3.97 (2H, s), 1.72 (2H, s).
51% With hydrogenchloride; hydrogen In ethanol; water for 2 h; A solution of 5-chloropicolinonitrile (3.8 g, 27.43 mmol), conc. HCl (3 mL) and 10percent Pd-C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2 h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4.x.25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51percent yield). LCMS (M+H) calcd for C6H8ClN2: 143.04; found: 143.07. 1HNMR (500 MHz, CDCl3) δ ppm: 8.56-8.51 (1 H, br d), 7.66-7.60 (1 H, m), 7.28-7.14 (1 H, m), 3.97 (2H, s), 1.72 (2H, s).
51% With hydrogenchloride; hydrogen In ethanol; water for 2 h; (5-Chloropyridin-2-yl)methanamine. A solution of 5-chloropicolinonitrile (3.8 g, 27.43 mmol), conc. HCl (3 mL) and 10percent Pd-C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2 h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4.x.25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51percent yield). LCMS (M+H) calcd for C6H8ClN2: 143.04. found: 143.07. 1HNMR (500 MHz, CDCl3) δ ppm: 8.56-8.51 (1H, br d), 7.66-7.60 (1H, m), 7.28-7.14 (1H, m), 3.97 (2H, s), 1.72 (2H, s).
51%
Stage #1: With hydrogenchloride; hydrogen In ethanol; water for 2 h;
Stage #2: With sodium hydrogencarbonate In ethanol; water
(5-Chloropyridin-2-yl)methanamine. A solution of 5-chloropicolinonitrile(3.8 g, 27.43 mmol), cone. HCl (3 mL) and 10percent Pd-C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4 X 25 mL). The combined CH2Cl2 layers were dried <n="142"/>(Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51percent yield). LCMS (M+H) calcd for C6H8ClN2: 143.04; found: 143.07. 1HNMR (500 MHz, CDCl3) δ ppm: 8.56-8.51 (IH, br d), 7.66-7.60 (IH, m), 7.28-7.14 (IH, m), 3.97 (2H, s), 1.72 (2H, s).

Reference: [1] Patent: US2005/267105, 2005, A1, . Location in patent: Page/Page column 63
[2] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 29
[3] Patent: US2007/129379, 2007, A1, . Location in patent: Page/Page column 21-22
[4] Patent: WO2007/64316, 2007, A1, . Location in patent: Page/Page column 140 - 141
  • 18
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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
  • 19
  • [ 626-60-8 ]
  • [ 7677-24-9 ]
  • [ 89809-64-3 ]
  • [ 38180-46-0 ]
  • [ 68325-15-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 20
  • [ 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
  • 21
  • [ 626-60-8 ]
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  • [ 89809-64-3 ]
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Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737
  • 22
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  • [ 209526-98-7 ]
Reference: [1] Patent: US2007/4772, 2007, A1,
  • 23
  • [ 89809-64-3 ]
  • [ 327056-62-2 ]
YieldReaction ConditionsOperation in experiment
72% at 210 - 220℃; for 4 h; Preparation 84; 2-Cyano-5-fluoropyridine; Add in a 5-L 3-neck roundbottom equipped with overhead stirrer, reflux condenser, thermometer, and N2 line, 5-chloro-2-cyanopyridine (193.0 g, 1. 39 mol) and 1-methyl-2-pyrrolidinone (NMP, 2L). Heat the mixture and stir at 210-220 ° C for 4 h. Cool the reaction mixture to room temperature, stir overnight, and filter. Wash the filter cake with ethyl ether (1L). Extract the filtrate with water (6L) and ethyl ether (3 X 5L). Combine the organics and back-extract with water (8L) and dry over magnesium sulfate. Concentrate at 25-30 ° C to give an oily semi-solid, 193 g. Chromatograph over flash silica gel (5percent ethyl acetate in hexanes gradually increasing to 10percent ethyl acetate in hexanes) to provide the title compound as a white solid. Dissolve the solid in ethyl ether, filter, and add hexanes. Concentrate to low volume to provide a primary crop of pure title compound, 60 g. Repeat the process of crystallization on the filtrate to provide a second crop of highly pure title compound, 24.0 g. (Concentrate the final filtrate to a white solid of product of good quality, and re-chromatograph, conditions as above, to provide an additional 38.6 g of material. ) Obtain a total yield of title compound of 122.4 g, 72percent ; 1H NMR (CDCl3) 5 8.59 (d, J= 3.0 Hz, 1H), 7.75 (m, 1H), 7.55 (m, 1H).
48% With potassium fluoride In 1-methyl-pyrrolidin-2-one A mixture of 2-cyano-5-chloropyridine (1 g, 7.22 mmol) and potassium fluoride (1.26 g, 21.68 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was heated at reflux for 18 hours.
After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine.
The organic solvents were then removed in vacuo.
Silica gel chromatography of the residue afforded 425 mg (48percent) of 2-cyano-5-fluoropyridine.
Reference: [1] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 75-76
[2] Patent: US2003/55085, 2003, A1,
  • 24
  • [ 89809-64-3 ]
  • [ 75-16-1 ]
  • [ 94952-46-2 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: at -63 - 20℃; for 2.25 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether for 4 h;
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; diethyl ether
a) l-(5-Chloropyridin-2-yl)ethanone5-Chloropyridine-2-carbonitxile (10.7 g, 77 mmol) was dissolved in diethyl ether (65 mL) and THF (35 mL) under a nitrogen atmosphere. The mixture was cooled until the internal temperature was -63 0C. Methylmagnesium bromide (3M in THF, 35 mL, 105 mmol) was added over 30 min. The reaction mixture was then left stirring at -60 °C for 45 min and was then warmed to room temperature. THF (50 mL) was added to dissolve any precipitated material and the reaction mixture was stirred for 1 h. 2M HCl aq. (100 mL) was added and the reaction mixture was stirred for 4 h. The pH was then adjusted to 7 with sodium bicarbonate. The phases were separated and the product extracted from the aqueous phase with DCM. The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The product was purified by flash column chromatography (eluent heptane:EtoAc gradient) to yield 7.9 g (64percent yield) of the title compound.1R NMR (300 MHz, CDCl3) δ ppm 8.62 (m, IH); 8.00 (m, IH); 7.80 (m, IH); 2.70 (s, 3H).
64%
Stage #1: at -63 - 20℃; for 2.25 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether for 4 h;
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; diethyl ether
a) 1 - (5- Chloropyridin-2-yl)ethanone5-Chloropyridine-2-carbonitrile (10.71 g, 77 mmol) was dissolved in diethylether (65 mL) and THF (35 mL) under a nitrogen atmosphere. The mixture was cooled until the internal temperature was -63 °C. Methyl magnesium bromide (3M in THF, 35 mL, 105 mmol) was added over 30 min. The reaction mixture was then left stirring at -60 0C for 45 min and was then warmed to room temperature. 50 mL of THF was added to dissolve any precipitated material. After 1 h at room temperature the reaction was judged complete by HPLC. 2M hydrochloric acid (aq., 100 mL) was added and the reaction mixture was stirred for 4 h. pH was adjusted to 7 with sodium bicarbonate. The phases were separated and the product extracted from the aqueous phase twice with DCM. The combined organise extracts were dried over sodium sulphate and concentrated in vacuo. The product was purified by column chromatography (eluent heptane: ethyl acetate gradient) to yield 7.9 g (64percent yield) of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.62 (m, IH); 8.00 (m, IH); 7.80 (m, IH); 2.70 (s, 3H).
Reference: [1] Patent: WO2008/39139, 2008, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2008/39138, 2008, A1, . Location in patent: Page/Page column 28
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