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[ CAS No. 27398-39-6 ] {[proInfo.proName]}

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Chemical Structure| 27398-39-6
Chemical Structure| 27398-39-6
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Product Details of [ 27398-39-6 ]

CAS No. :27398-39-6 MDL No. :MFCD01318438
Formula : C5H3ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PMRPVXLESNMKLG-UHFFFAOYSA-N
M.W : 158.54 Pubchem ID :1501900
Synonyms :

Calculated chemistry of [ 27398-39-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.0
TPSA : 63.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.6
Log Po/w (XLOGP3) : 0.6
Log Po/w (WLOGP) : 0.83
Log Po/w (MLOGP) : -0.61
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 0.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.18 mg/ml ; 0.0264 mol/l
Class : Very soluble
Log S (Ali) : -1.5
Solubility : 5.03 mg/ml ; 0.0317 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.63
Solubility : 3.72 mg/ml ; 0.0234 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 27398-39-6 ]

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 [ 27398-39-6 ]

* 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 [ 27398-39-6 ]
  • Downstream synthetic route of [ 27398-39-6 ]

[ 27398-39-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 27398-39-6 ]
  • [ 18107-18-1 ]
  • [ 27825-21-4 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 67, p. 16990 - 16997
[2] Patent: WO2016/65585, 2016, A1, . Location in patent: Page/Page column 48
[3] Patent: WO2016/89721, 2016, A1, . Location in patent: Page/Page column 40
[4] Patent: WO2016/100161, 2016, A1, . Location in patent: Page/Page column 54-55
[5] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 38; 39
  • 2
  • [ 67-56-1 ]
  • [ 27398-39-6 ]
  • [ 27825-21-4 ]
YieldReaction ConditionsOperation in experiment
100 mg With diazomethyl-trimethyl-silane In dichloromethane at 20℃; for 2 h; To a solution of 3-.chioropyrazine-.2—carboxyiic acid (100 mg, 0.63 mmoi) in DCM/MeOFI (2 mL : ().2 mL) was added TMSCHN2 (0.47 mL, 0.95 mmoi) at RT and the resulting mixture stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers werewashed with brine, dried over Na2 SO4, filtered and concentrated in vacuo to give the title compound (100 mg) as a colorless oil. LRMS mIz (M+H) 173.0 found, 173.0 required. Step 2: Methyl 3-.pyridin-.2-.yl)pyrazine—2--carboxyiate (M2)
Reference: [1] Patent: WO2016/100157, 2016, A2, . Location in patent: Page/Page column 54; 55
[2] Patent: WO2016/101119, 2016, A1, . Location in patent: Page/Page column 42; 43
  • 3
  • [ 189999-35-7 ]
  • [ 27398-39-6 ]
  • [ 217-68-5 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 26, p. 3239 - 3242
  • 4
  • [ 27398-39-6 ]
  • [ 89283-32-9 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With triethylamine; methyl chloroformate In tetrahydrofuran for 0.5 h; Cooling with ice
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water for 1 h; Cooling with ice
3-Chloropyrazine-2-carboxylic acid (2.97 g, 18.73 mmol, 1 eq.) was dissolved in tetrahydrofuran (75 mL). The solution was stirred in an ice bath and triethylamine (5.2 mL, 37.5 mmol, 2 eq.) was added followed by addition of methyl chloroformate (1.74 mL, 22.5 mmol, 1.2 eq.) dropwise. After 30 m, the reaction was filtered and the solid rinsed with more tetrahydrofuran (10 mL). The tetrahydyofuran solution was stirred in an ice bath and a suspension of sodium borohydride (1.4 g, 37.5 mmol, 2 eq.) in water (3 mL) was added. After 1 h, a saturated aqueous ammonium chloride solution (100 mL) was added to the reaction and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic phases were washed with a saturated aqueous sodium chloride solution (25 mL) and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel chromatography (5 - 70percent ethyl acetate/hexanes) to give (3-chloropyrazin-2-yl)methanol (0.84 g, 31percent) as a faintly colored oil.
22%
Stage #1: With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In water at 0℃; for 1 h;
102901 To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) andTEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL,15.20 mmol, 1.2 eq.) atO °C. The mixture was stirred at 0°C for 10 mm and filtered. To thisfiltrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0 °C. The mixture was stirred at 0 °C for 1 h, quenched with NH4C1 (aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2- yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) 8.58 (d,J 2.5 Hz,1H), 8.38 (d,J= 2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.
Reference: [1] Patent: WO2016/160755, 2016, A1, . Location in patent: Page/Page column 30
[2] Patent: WO2013/102145, 2013, A1, . Location in patent: Paragraph 0290
  • 5
  • [ 79-22-1 ]
  • [ 27398-39-6 ]
  • [ 89283-32-9 ]
YieldReaction ConditionsOperation in experiment
22%
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1 h;
Step 1
To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) and TEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL, 15.20 mmol, 1.2 eq.) at 0° C.
The mixture was stirred at 0° C. for 10 min and filtered.
To this filtrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0° C.
The mixture was stirred at 0° C. for 1 h, quenched with NH4Cl(aq) solution, and extracted with EtOAc twice.
The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2-yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) δ 8.58 (d, J=2.5 Hz, 1H), 8.38 (d, J=2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.
Reference: [1] Patent: US2015/344483, 2015, A1, . Location in patent: Paragraph 0536; 0537
  • 6
  • [ 55557-52-3 ]
  • [ 27398-39-6 ]
Reference: [1] Molecules, 2015, vol. 20, # 5, p. 8687 - 8711
[2] Molecules, 2017, vol. 22, # 3,
  • 7
  • [ 27825-21-4 ]
  • [ 27398-39-6 ]
Reference: [1] Magnetic Resonance in Chemistry, 2009, vol. 47, # 7, p. 617 - 624
  • 8
  • [ 14508-49-7 ]
  • [ 124-38-9 ]
  • [ 27398-39-6 ]
Reference: [1] Synthesis, 1988, # 11, p. 881 - 884
  • 9
  • [ 20737-42-2 ]
  • [ 27398-39-6 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 2, p. 299 - 301
  • 10
  • [ 20737-42-2 ]
  • [ 27398-39-6 ]
Reference: [1] Magnetic Resonance in Chemistry, 2009, vol. 47, # 7, p. 617 - 624
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