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[ CAS No. 40381-90-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 40381-90-6
Chemical Structure| 40381-90-6
Chemical Structure| 40381-90-6
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Product Details of [ 40381-90-6 ]

CAS No. :40381-90-6 MDL No. :MFCD03411341
Formula : C6H2Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :LFCADBSUDWERJT-UHFFFAOYSA-N
M.W : 173.00 Pubchem ID :12605538
Synonyms :
2,6-Dichloropyridine-3-carbonitrile
Chemical Name :2,6-Dichloropyridine-3-carbonitrile

Calculated chemistry of [ 40381-90-6 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 38.97
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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.61
Consensus Log Po/w : 1.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.512 mg/ml ; 0.00296 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.969 mg/ml ; 0.0056 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.0793 mg/ml ; 0.000458 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 40381-90-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338+P310-P403+P233-P405 UN#:3439
Hazard Statements:H301+H311+H331-H315-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40381-90-6 ]

* 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 [ 40381-90-6 ]
  • Downstream synthetic route of [ 40381-90-6 ]

[ 40381-90-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 40381-90-6 ]
  • [ 62068-78-4 ]
YieldReaction ConditionsOperation in experiment
73% at 90℃; for 1 h; To 2,6-dichloronicotinonitrile 1 (1.73 g, 10 mmol) was added cone H2SO4 (10 mL) and water (2 mL). The mixture was heated to 90°C and stirred for 1 h. After cooling to room temperature, the solution was poured into ice-cold water, then adjusted to PH = 8 with ammonia water. The precipitate was filtered, washed with water (20 mL) and dried under vacuum to afford the title compound as an brown solid (1.4 g, 73percent). MS (ESI): m/z = 191.1 [M+H]+.
73% With sulfuric acid In water at 90℃; for 1 h; The compound 2,6-dichloro-nicotinonitrile 1a (1.73 g, 10 mmol), concentrated sulfuric acid (10 mL) and water (2 mL) were mixed,Heated to 90 ° C and stirred for 1 hour. The mixture was cooled to room temperature and the reaction mixture was poured into an ice-water bath and the pH was adjusted to 8 with aqueous ammonia. TooThe filter cake was washed with water and dried to give the desired product 2,6-dichloroacidamide 1b (1.4 g, solid) in 73percent yield
Reference: [1] Patent: WO2015/48662, 2015, A2, . Location in patent: Page/Page column 37
[2] Patent: CN107226805, 2017, A, . Location in patent: Paragraph 0097; 0098; 0099; 0100; 0101
  • 2
  • [ 76175-82-1 ]
  • [ 40381-90-6 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; trifluoroacetic anhydride In dichloromethane Preparation of 2,6-dichloropyridine-3-carbonitrile
To a mixture of 2,6-dichloro-3-acetamidopyridine (6.3 g, 55percent pure) and pyridine (4.93 ml, 61 mmole) in dichloromethane (100 ml), trifluoroacetic anhydride (4.23 ml, 30 mmole) was added.
The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure.
The crude product was purified by flash chromatography, eluding with 85percent hexane: 15percent ethyl acetate to give a pale yellow product (1.77 g, 90percent).
HPLC: 10.26 min (90percent pure)
MS: MH+=172.9 C6H2C12N2 171.9 g/mol
Reference: [1] Patent: US2002/156087, 2002, A1,
  • 3
  • [ 91467-46-8 ]
  • [ 40381-90-6 ]
Reference: [1] Patent: US2007/225282, 2007, A1, . Location in patent: Page/Page column 31-32
  • 4
  • [ 62068-78-4 ]
  • [ 40381-90-6 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 35, p. 6940 - 6952
  • 5
  • [ 55304-73-9 ]
  • [ 40381-90-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 1, p. 266 - 273
  • 6
  • [ 35441-10-2 ]
  • [ 40381-90-6 ]
Reference: [1] Angewandte Chemie, 1980, vol. 92, # 5, p. 390 - 391
  • 7
  • [ 38496-18-3 ]
  • [ 40381-90-6 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 35, p. 6940 - 6952
  • 8
  • [ 58584-83-1 ]
  • [ 40381-90-6 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 35, p. 6940 - 6952
  • 9
  • [ 24388-23-6 ]
  • [ 40381-90-6 ]
  • [ 43083-14-3 ]
YieldReaction ConditionsOperation in experiment
63.4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 90℃; for 6 h; Inert atmosphere 0.865 g of 2,6-dichloro-nicotine and 1.021 g of 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborane were dissolved in 60 mlEthylene glycol dimethyl ether, 20 ml of an aqueous solution of sodium hydrogencarbonate (1 mole per liter) and 0.366 g of [1,1'-bis (diphenylphosphineBased ferrocene] dichloride, the temperature was raised to 90 ° C under argon, and the mixture was heated for 6 hours. The reaction solution was separated,The aqueous phase was extracted with ethyl acetate and the organic phases were combined and washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filteredThe residue was purified by column chromatography (petroleum ether: ethyl acetate = 99: 1-95: 5, V / V) to give 0.680 g of a white solidRate of 63.4percent.
Reference: [1] Patent: CN106146493, 2016, A, . Location in patent: Paragraph 0164; 0165; 0166; 0167
  • 10
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
  • 11
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
  • 12
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 121643-47-8 ]
  • [ 121643-46-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Patent: US2015/291629, 2015, A1, . Location in patent: Paragraph 0800
[3] Patent: CN108003161, 2018, A, . Location in patent: Paragraph 0489; 0491-0493
  • 13
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 121643-46-7 ]
YieldReaction ConditionsOperation in experiment
19% at 60℃; for 12 h; To a stirred solution of 2,6-dichioronicotinonitrile (050 g, 2.89 mmoi) in MeOH (10 mL)was added sodium methanolate (0.62 g, 2.89 mmol) at ambient temperature. The reactionmixture was stirred at 60 °C for 12 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure, diluted with water (40 ml) and extracted with ethyl acetate (2 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by preparativeHPLC [Xbridge Phenyl (21.2 x 250 ID) 5 micron; Solvent A: 0.1percent TFA, Solvent B:Acetonitrile, Gradient: 5-25percent B over 25 mm, Flow: 20 mL/minj to 23A (0.48 g, 19percent) as an off white solid. ‘HNMR (400 MHz, CDCI3) ppm 4.08 (s, 3 H). 7.01 -- 7.03 (d, J= 7.2 Hz, I H), 7.80 7.82 (s, J= 8.0 Hz, IH). LCMS MethodD): retention time 1.94 mm, [M+H] 169.2.
Reference: [1] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 100
  • 14
  • [ 40381-90-6 ]
  • [ 52471-07-5 ]
Reference: [1] Patent: WO2017/98328, 2017, A2,
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