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[ CAS No. 55557-52-3 ] {[proInfo.proName]}

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Chemical Structure| 55557-52-3
Chemical Structure| 55557-52-3
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Product Details of [ 55557-52-3 ]

CAS No. :55557-52-3 MDL No. :MFCD00219653
Formula : C5H2ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :SDLFAEGTVBPHBK-UHFFFAOYSA-N
M.W : 139.54 Pubchem ID :292465
Synonyms :

Calculated chemistry of [ 55557-52-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 31.76
TPSA : 49.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 1.29
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.36 mg/ml ; 0.00975 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.64 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.33
Solubility : 0.657 mg/ml ; 0.00471 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 55557-52-3 ]

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 [ 55557-52-3 ]

* 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 [ 55557-52-3 ]
  • Downstream synthetic route of [ 55557-52-3 ]

[ 55557-52-3 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 768-36-5 ]
  • [ 19847-12-2 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 2
  • [ 25594-31-4 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 3
  • [ 55557-52-3 ]
  • [ 25911-65-3 ]
  • [ 75018-05-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 817 - 819
  • 4
  • [ 67-56-1 ]
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  • [ 25911-65-3 ]
  • [ 75018-05-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 817 - 819
  • 5
  • [ 55557-52-3 ]
  • [ 21279-62-9 ]
YieldReaction ConditionsOperation in experiment
80% With dihydrogen peroxide; sodium hydroxide In water at 50 - 60℃; for 2.5 h; The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 °C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 °C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 °C. The pH was adjusted and regulated around a value of 9 using an 8percent solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 °C. The reaction was stopped after 2.5 h and was cooled to 5 °C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].
80% at 50 - 55℃; for 3 h; The starting compound 3-chloropyrazine-2-carboxamide was prepared via partial hydrolysis of the nitrile group of 3-chloropyrazine-2-carbonitrile (Fluorochem, Co., Hadfield, Derbyshire, UK). A mixture of concentrated (30percent) hydrogen peroxide (29 mL) and water (195 mL) was prepared and alkalinized with an 8percent (w/v) solution of sodium hydroxide to obtain a solution with pH 9. The carbonitrile (104 mmol) was then added portionwise into the heated (50 °C) mixture over a period of 30 min. The whole mass was stirred for an additional 2.5 h at 55 °C while the pH was periodically monitored and alternatively adjusted to the value of 9 by adding a few drops of 8percent NaOH solution. The reaction mixture was cooled in a fridge to initiate crystallization. The crude product was recrystallized from ethanol [27]. The yield of this reaction was approximately 80percent.
Reference: [1] Molecules, 2014, vol. 19, # 7, p. 9318 - 9338
[2] Molecules, 2017, vol. 22, # 2,
  • 6
  • [ 98-96-4 ]
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  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 7
  • [ 768-36-5 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 8
  • [ 25594-31-4 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 9
  • [ 98-96-4 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 10
  • [ 768-36-5 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 11
  • [ 25594-31-4 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 12
  • [ 19847-12-2 ]
  • [ 55557-52-3 ]
YieldReaction ConditionsOperation in experiment
51% With sulfuryl dichloride In N,N-dimethyl-formamide; toluene at 20℃; for 5.6 h; Cooling with ice To a solution of pyrazine-2-carbonitrile 13 (6.90 g, 65.65 mmol) in toluene (48 mL) and DMF (5 mL) was added sulfuryl chloride (21.2 mL, 260.8 mmol) over 10 min. The reaction mixture was stirred for 30 min in an ice bath, then allowed to warm up to room temperature gradually, after which it was stirred for 5 h. The toluene layer was decanted, and the reddish oil residue was extracted three times with diethyl ether. The combined toluene and ether layers were quenched with ice water and cooled in an ice bath. The combined layers were then neutralized with solid NaHCO3, then separated, and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated under reduced pressure to afford the title compound. The crude product was purified by silica gel chromatography (eluent: 100percent dichloromethane) to give 3-chloropyrazine-2-carbonitrile 14 as a white powder (4.7 g, 51percent). Rf = 0.76 (dichloromethane); mp 44-46 °C (lit. [14] : 47-48 °C); IR (KBr) νmax (cm-1): 3088 (νCHar), 2242 (νCN), 1377 (νC=C), 1087 (νC-N); 1H NMR (400 MHz, DMSO-d6): δ 8.91 (d, 1H, J = 2.4 Hz, H-6), 8.88 (d, 1H, J = 2.4 Hz, H-5); 13C NMR (100 MHz, DMSO-d6): δ 150.67 (C-3), 147.97 (C-5), 144.26 (C-6), 129.87 (C-2), 114.66 (CN); MS (ESI) m/z (percent): 140.3 (100) [M + H]+, 142.3 (40) [M + H + 2]+. Anal. calcd for C5H2ClN3: C, 43.04; H, 1.44; N, 30.11. Found: C, 43.18; H, 1.45; N, 30.16.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 171 - 183
[2] Patent: EP1582521, 2005, A1, . Location in patent: Page/Page column 133-134
[3] Magnetic Resonance in Chemistry, 2009, vol. 47, # 7, p. 617 - 624
  • 13
  • [ 55321-99-8 ]
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YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; trichlorophosphate In chlorobenzene at 0 - 90℃; At 0 , a solution of 3-hydroxy-2-carboxamide (5g, 37mmol) in chlorobenzene (20 mL) was added dropwise phosphorus oxychloride (2mL, 40mmol) and diisopropylethylamine (3.5mL, 80mmol), dropwise addition, the reaction mixture was stirred overnight at 90 placed.After the reaction, the reaction solution was concentrated under reduced pressure the reaction solution, the residue was diluted with 20mL water, (20mL x 3) and extracted with EtOAc, the combined organic phases were dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the residue was purified by silica gel column chromatography ( eluant: PE / EtOAc (V / V) = 10/1) to give the title compound as a white solid (4.5g, 79percent).
Reference: [1] Patent: CN104447584, 2016, B, . Location in patent: Paragraph 0138; 0139; 0140
  • 14
  • [ 55321-99-8 ]
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YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; trichlorophosphate In chlorobenzene at 0 - 90℃; At 0 , a solution of 3-hydroxy-2-carboxamide (5g, 37mmol) in chlorobenzene (20 mL) was added phosphorus oxychloride (2mL, 40mmol)And diisopropylethylamine (3.5mL, 80mmol), dropwise addition, the reaction mixture was stirred overnight at 90 placed. After the reaction, the reaction solution under reduced pressureConcentrated, then diluted with 20mL of water was added, the resulting mixture was extracted with EtOAc (20mL x 3), the combined organic phases were dried over anhydrous sodium sulfate,Then filtered and concentrated under reduced pressure, and finally the residue was purified by silica gel column chromatography (eluent: PE / EtOAc (V / V) = 10/1) to give a white solidThe title compound (4.5g, 79percent).
Reference: [1] Patent: CN104447583, 2016, B, . Location in patent: Paragraph 0172; 0173; 0174; 0175
  • 15
  • [ 2423-65-6 ]
  • [ 98-96-4 ]
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Reference: [1] Patent: US4293552, 1981, A,
  • 16
  • [ 7677-24-9 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2877 - 2882
  • 17
  • [ 98-96-4 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 18
  • [ 768-36-5 ]
  • [ 55557-52-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 19
  • [ 768-36-5 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 20
  • [ 25594-31-4 ]
  • [ 19847-12-2 ]
  • [ 6863-74-7 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  • 21
  • [ 55557-52-3 ]
  • [ 27398-39-6 ]
Reference: [1] Molecules, 2015, vol. 20, # 5, p. 8687 - 8711
[2] Molecules, 2017, vol. 22, # 3,
  • 22
  • [ 623-51-8 ]
  • [ 55557-52-3 ]
  • [ 56881-21-1 ]
YieldReaction ConditionsOperation in experiment
68.5% With sodium carbonate In ethanol for 4.5 h; Reflux Step 7: synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7)A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5 percent). 1H-NMR (400 MHz, CDC13) 1.42 (t, J= 7.2 Hz, 3H), 4.40 (q, J= 7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J= 2.2 Hz, 1H), 8.63 (d, J= 2.2 Hz, 1H).
68.5% With sodium carbonate In ethanol for 4.5 h; Reflux Step 7:
synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7)
A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5 h.
Quenched with water (1.5 L) and stirred for 30 min.
The resulting precipitate was collected and washed with water.
The residue was dissolved in diethyl ether and a black precipitate was filtrated off.
Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5percent).
1H-NMR (400 MHz, CDCl3) 1.42 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3643 - 3647
[2] Tetrahedron, 2008, vol. 64, # 7, p. 1333 - 1344
[3] Patent: WO2011/147764, 2011, A1, . Location in patent: Page/Page column 27
[4] Patent: US2013/79341, 2013, A1, . Location in patent: Paragraph 0110
[5] Journal of Heterocyclic Chemistry, 1975, vol. 12, p. 513 - 516
[6] Patent: WO2016/144849, 2016, A1, . Location in patent: Page/Page column 28
  • 23
  • [ 55557-52-3 ]
  • [ 272-60-6 ]
Reference: [1] Heterocycles, 1982, vol. 19, # 2, p. 339 - 342
[2] Monatshefte fuer Chemie, 1982, vol. 113, p. 731 - 744
[3] Patent: WO2017/133657, 2017, A1,
  • 24
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  • [ 111042-89-8 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2587 - 2601
  • 25
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  • [ 55557-52-3 ]
Reference: [1] Patent: US4293552, 1981, A,
  • 26
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  • [ 81411-79-2 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 18, p. 4941 - 4946
  • 27
  • [ 55557-52-3 ]
  • [ 81411-68-9 ]
Reference: [1] Heterocycles, 1982, vol. 19, # 2, p. 339 - 342
[2] Monatshefte fuer Chemie, 1982, vol. 113, p. 731 - 744
  • 28
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  • [ 81411-64-5 ]
Reference: [1] Monatshefte fuer Chemie, 1982, vol. 113, p. 731 - 744
[2] Heterocycles, 1982, vol. 19, # 2, p. 339 - 342
[3] Patent: WO2017/133657, 2017, A1, . Location in patent: Page/Page column 67; 68
  • 29
  • [ 55557-52-3 ]
  • [ 939412-86-9 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 36 h; To a solution of 3-chloropyrazine-2-carbonitrile (Compound 101) (6.00 g, 43.0 mmol, 1.0 equiv.) In acetic acid (50 mL) was added Raney nickel (4.00 g) In the hydrogen ball under the room temperature reaction for 1.5 days. The reaction solution was filtered and the filtrate was taken dry and the residue was spin-fed with toluene (40 mL), 1 N HCl (15 mL) and toluene (40 mL) The residue was dissolved in tetrahydrofuran (30 mL), filtered, the cake was spin dried, To give (3-chloropyrazin-2-yl) methanamine hydrochloride (8.75 g, yield: 100percent). Black solid;
153.5 g
Stage #1: With hydrogen; acetic acid In water at 20℃;
Stage #2: With hydrogenchloride In diethyl ether; ethyl acetate at 20℃; Cooling with ice
To a solution of 3-chloropyrazine-2-carbonitrile (160 g, 1.147 mol) in acetic acid (1.5 L) was added Raney Nickel (50percent slurry in water, 70 g, 409 mmol). The resulting mixture was stirred under 4 bar hydrogen at room temperature overnight. Raney Nickel was removed by filtration over decalite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50°C and cooled on an ice-bath. 2M hydrogen chloride solution in diethyl ether (1.14 L) was added in 30 min. The mixture was allowed to stir at room temperature over weekend. The crystals were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40°C. The product brown solid obtained was dissolved in methanol at 60°C. The mixture was filtered and partially concentrated, cooled to room temperature and diethyl ether (1000 ml) was added. The mixture was allowed to stir at room temperature overnight. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40°C to give 153.5 g of (3-chloropyrazin-2-yl)methanamine. hydrochloride as a brown solid (74.4 percent, content 77 percent).
Reference: [1] Patent: CN106588937, 2017, A, . Location in patent: Paragraph 0152; 0158; 0159
[2] Patent: WO2013/10869, 2013, A1, . Location in patent: Page/Page column 25
[3] Patent: WO2013/10868, 2013, A1, . Location in patent: Page/Page column 29-30
[4] Patent: EP2548877, 2013, A1, . Location in patent: Paragraph 0143
[5] Patent: WO2016/24227, 2016, A1, . Location in patent: Paragraph 00207
[6] Patent: WO2017/100591, 2017, A1, . Location in patent: Paragraph 00352
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