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[ CAS No. 1082843-70-6 ] {[proInfo.proName]}

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Chemical Structure| 1082843-70-6
Chemical Structure| 1082843-70-6
Structure of 1082843-70-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1082843-70-6 ]

CAS No. :1082843-70-6 MDL No. :MFCD13193367
Formula : C4HBr2ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNZURIDUDWMEKQ-UHFFFAOYSA-N
M.W : 272.33 Pubchem ID :53350358
Synonyms :

Calculated chemistry of [ 1082843-70-6 ]

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 : 42.44
TPSA : 25.78 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 2.66
Log Po/w (MLOGP) : 1.36
Log Po/w (SILICOS-IT) : 3.07
Consensus Log Po/w : 2.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.78
Solubility : 0.0453 mg/ml ; 0.000166 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.28 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.97
Solubility : 0.029 mg/ml ; 0.000106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.45

Safety of [ 1082843-70-6 ]

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 [ 1082843-70-6 ]

* 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 [ 1082843-70-6 ]
  • Downstream synthetic route of [ 1082843-70-6 ]

[ 1082843-70-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1082843-70-6 ]
  • [ 1082843-72-8 ]
YieldReaction ConditionsOperation in experiment
66% at 100℃; Sealed tube [0955] Into a 250 mL sealed tube was placed compound90d (50.0 g, 184 mmol) andNH40H (150mL). The resultingmixture was stirred overnight at 100° C. Uponcooling, a solidwas collected by filtration and dried in an oven under reducedpressure to obtain the compound 90e as a grey solid (28.0 g,66percent yield), which was used in next step without furtherpurification.
Reference: [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0954-0955
[2] Patent: US2009/286798, 2009, A1, . Location in patent: Page/Page column 27
  • 2
  • [ 1082843-70-6 ]
  • [ 1082843-72-8 ]
Reference: [1] Patent: US2011/118269, 2011, A1, . Location in patent: Page/Page column 14
  • 3
  • [ 24241-18-7 ]
  • [ 1082843-70-6 ]
YieldReaction ConditionsOperation in experiment
83% With tert.-butylnitrite; titanium tetrachloride In dichloromethane at 20℃; for 2 h; [0953] To a solution of3,5-dibromopyrazin-2-amine (234g, 932 mmol) in DCM (700 mL) and titanium (IV) chloride(174 g, 926 mmol), tert-butyl nitrite (572 g, 5.55 mol) wasslowly added. The resulting mixture was stirred for 2 h atroom temperature and treated with water (500 mL). Theresulting mixture was extracted with DCM (3x500 mL). Thecombined organic layers were concentrated under reducedpressure. The resultant residue was purified by flash colunmchromatography on silica gel (EtOAc/petroleum ether (1:50v/v)) to obtain compound 90d as colorless oil (210 g, 83percentyield). Mass Spectrum (LCMS, ESI pos.): Calcd. forC4 HBr2ClN2 : 272.8 (M+H). found 272.6.
82% With tert.-butylnitrite; titanium tetrachloride In DCM at 0 - 20℃; Step 1: Synthesis of Compound (A') as Described in the General Reaction Scheme; 2-chloro-3,5-dibromo-pyrazineTo a well stirred solution of 2-amino-3,5-dibromopyrazine (3.21 g, 12.692 mmol) in DCM (20 1 mL) cooled to 0° C. is added TiCl4 (2.41 g, 12.692 mmol, 1.00 equiv.) in one portion, thus giving a dark red slurry. t-Butylnitrite (2.62 g, 25.385 mmol, 2.00 equiv.) is then added dropwise, causing the solution to turn bright yellow. The ice bath is then removed and the reaction is then allowed to proceed at room temperature. More TiCl4 (1.50 g, 1.2 equiv.) is added and the mixture is stirred further for one hour. At that point an orange solution has formed and LC-MS shows full conversion of the starting material to the desired product which ionises very poorly. Water (100 1 mL) is added to the reaction, forming an emulsion. DCM (50 1 mL) is added, and the DCM layer is separated, and the aqueous layer is further extracted with DCM (3.x.50 mL) until the DCM layer is colorless. The DCM layers are gathered, washed with brine and dried over anhydrous Na2SO4, to yield after solvent removal, compound A' (2.81 g, 82percent) as an orange oil, which is used as such in the following step.
Reference: [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0952-0953
[2] Patent: US2009/286798, 2009, A1, . Location in patent: Page/Page column 26-27
[3] Patent: US2011/118269, 2011, A1, . Location in patent: Page/Page column 14
[4] Patent: WO2014/1377, 2014, A1, . Location in patent: Page/Page column 153; 154
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