[ CAS No. 59489-71-3 ] {[proInfo.proName]}

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2D 3D

Structure of 59489-71-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 59489-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59489-71-3 ]

SDS Specification

Alternatived Products of [ 59489-71-3 ]

Product Details of [ 59489-71-3 ]

CAS No. :	59489-71-3	MDL No. :	MFCD00235015
Formula :	C₄H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	Br(C₄H₂N₂)NH₂	InChI Key :	KRRTXVSBTPCDOS-UHFFFAOYSA-N
M.W :	174.00	Pubchem ID :	599539
Synonyms :

Calculated chemistry of [ 59489-71-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.14
TPSA :	51.8 ?2

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) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.09
Log Po/w (XLOGP3) :	0.73
Log Po/w (WLOGP) :	0.83
Log Po/w (MLOGP) :	-0.26
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	0.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.93
Solubility :	2.03 mg/ml ; 0.0116 mol/l
Class :	Very soluble
Log S (Ali) :	-1.4
Solubility :	6.98 mg/ml ; 0.0401 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.14
Solubility :	1.25 mg/ml ; 0.00721 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.38

Safety of [ 59489-71-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 59489-71-3 ]

* 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 [ 59489-71-3 ]
Downstream synthetic route of [ 59489-71-3 ]

[ 59489-71-3 ] Synthesis Path-Upstream 1~1

1
[ 59489-71-3 ]
[ 1062608-42-7 ]

Yield	Reaction Conditions	Operation in experiment
25.1%	With N-iodo-succinimide In 1,4-dioxane at 80℃; for 16 h;	To the solution of 2 (10.0 g, 57.47 mmol) in 1,4-dioxane (100 mL) was added N- iodosuccinimide (15.5 g, 68.96 mmol). The reaction mixture was heated to 800 C for 16 h, cooled to RT and concentrated under vacuum to remove 1,4-dioxane. 50 mL of water was added and extracted with dichloromethane (50 mL X 4), washed with water (20 mL X 3), dried over sodium sulfate and concentrated under reduced vacuum. Crude product was purified by flash chromatography using 20-30percent ethyl acetate in petroleum ether to afford compound 2b (4.3 g, 25.1percent). 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1H), 6.76 (s, 2H).
7.56%	With iodine In dimethyl sulfoxide at 20 - 100℃; for 4 h;	To a solution of compound (ii) (1.98 g, 11.46 mmol) in DMSO (20 ml) was added iodine crystals (3.49 g, 13.75 mmol) at RT and the resulting mixture was heated to 100°C for 4 h and then stirred at RT for 12 h. Water (20 ml) was then added and the reaction mixture was extracted with ethyl acetate (60 ml X 4). Combined organic layers were washed with water (10 ml X 3), saturated sol. of sodium metabisulphite (5 ml X till Iodine color disappears), Brine solution (10 ml), dried over anhydrous Na₂S0₄ and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using ethyl acetate in petroleum ether as an eluent to yield compound (iii) (260 mg, 7.56percent) as white solid.

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8860 - 8871
[2] Patent: WO2017/9773, 2017, A1, . Location in patent: Page/Page column 19
[3] Patent: WO2013/121387, 2013, A1, . Location in patent: Page/Page column 30

[ 59489-71-3 ] Synthesis Path-Downstream 1~7

1
[ 59489-71-3 ]
[ 151-50-8 ]
CuCN [ No CAS ]
[ 89323-09-1 ]
[ 40155-43-9 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 2798

2
[ 59489-71-3 ]
[ 197223-39-5 ]
[ 1220531-17-8 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 1401 - 1403

3
[ 59489-71-3 ]
[ 133997-05-4 ]
[ 1353879-67-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate; In water; acetonitrile; for 6h;Reflux;	Pd(OAc)2 (0.232 mg, 1.032 mumol), and S-Phos (2.89 mg, 7.03 mumol) were added to a suspension of K2CO3 (243 mg, 1.758 mmol), 5-bromopyrazin-2-amine (61.2 mg, 0.352 mmol), and <strong>[133997-05-4](4-octylphenyl)boronic acid</strong> (107 mg, 0.457 mmol) (prepared according to Ishi-I, T. et al.49) in acetonitrile/water (1.5:1). The suspension was degassed for 5 min and then refluxed for 6 h. The reaction mixture was extracted with EtOAc, washed with brine, dried with MgSO4 and filtered. After evaporation of the organic solvent under reduced pressure, the resulting residue was purified by column chromatography over silica gel (100% hexanes to 50/50 hexanes/EtOAc) to provide an orange solid (95% yield). 1H NMR (400 MHz, CDCl3) delta 8.45 (s, 1H), 8.04 (s, 1H), 7.78 (d, J = 8.1 Hz, 2H), 7.26 (d, J = 8.1 Hz, 2H), 4.82 (br s, 1H), 2.64 (t, J = 7.7 Hz, 2H), 1.63 (m, 2H), 1.38-1.20 (m, 8H), 0.88 (t, J = 6.6 Hz, 3H); 13C NMR (101 MHz, CDCl3) delta 152.8, 143.2, 143.0, 138.4, 134.3, 131.8, 128.9, 125.5, 35.7, 31.9, 31.4, 29.5, 29.3, 29.2, 22.7, 14.1; HRMS (ESI+) m/z calcd for C18H26N3 [M+H]+ 284.2121, found 284.2136.The above amine was dissolved in 10 mL methanol and HCl (g) was bubbled through the solution for one minute. After evaporation of the methanol, diethyl ether was added and the solid filtered. It was washed with cold diethyl ether to yield the title compound as a pale yellow solid (95% yield).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 183 - 194

4
[ 389621-84-5 ]
[ 59489-71-3 ]
[ 1000067-96-8 ]

Yield	Reaction Conditions	Operation in experiment
44.88%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 20℃; for 16h;Inert atmosphere; Reflux;	To the solution of a 5-bromo-pyrazine-2-amine according to formula (1.5 g, 8.62 mmol) in 1 ,4-dioxane (20 ml) was added a boronic acid of formula (vi) such as 4-(morpholine- 4-carbonyl)phenylboronic acid (CombiBlocks) (2.046 g, 8.70 mmol) at RT and the resulting mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium (Il)chloride (423 mg, 0.60 mmol) and 1 M aqueous solution of potassium carbonate (10.34 ml, pre-purged with N2 gas) were added to the reaction mixture. The reaction mixture was heated to reflux for 16 h, cooled to RT and concentrated under vacuum. 5 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml X 4). Combined organic layers were washed with brine solution (5 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using 2% of MeOH in DCM as an eluent to yield a 5 -substituted pyrazine-2- amine of formula (vii) (1.1 g, 44.88%) as pale yellow solid.

Reference： [1]Patent: WO2013/121387,2013,A1 .Location in patent: Page/Page column 6

5
[ 59489-71-3 ]
[ 1217501-53-5 ]
[ 1612287-82-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 100.0℃; for 6.0h;Schlenk technique; Inert atmosphere;	General procedure: An oven dried resealable Schlenk tube was charged with 5-bromo-2-chloro-1H-pyrrolo[2,3-b]pyridine (Preparation 1c, 0.5 g, 2.07 mmol), (6-methoxy-4-methylpyridin-3-yl)boronic acid (Preparation 2, 0.35 g, 2.08 mmol), cesium carbonate (2.027 g, 6.22 mmol), 5.5 ml dioxane and 5.5 ml water. The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.085 g, 0.10 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 100 C. After 6h, the mixture was cooled and the solvent was removed in vacuo. Water was added and product was extracted with dichloromethane and organic layer was dried (Na2SO4). The residue was purified by flash chromatography (10%, dichloromethane-methanol) to give the title compound (0.353 g, 62% yield) as a solid. LRMS (m/z):274 (M+1)+. 5-Bromopyrazin-2-amine was treated with (2-methyl-4-(morpholinosulfonyl)-phenyl)boronic acid, cesium carbonate, [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane and dioxane as a solvent according to the method described in Preparation 3a. The crude was purified by flash chromatography (0% to 100%, hexane-ethyl acetate) to give the title compound (74% yield). LRMS (m/z): 335 (M+1)+

Reference： [1]Patent: EP2738172,2014,A1 .Location in patent: Paragraph 0108; 0186

6
[ 59489-71-3 ]
[ 33142-21-1 ]
6-bromoimidazo[1,2-a]pyrazine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641
[2]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 68
[3]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 346

7
[ 59489-71-3 ]
[ 915411-01-7 ]
5-(1H-indazol-7-yl)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.21 g		To a stirred suspension of 5-bromopyrazin-2-amine (CAS Number 59489-71 - 3; 0.100 g, 0.575 mmol) and 1 H-indazol-7-ylboronic acid (CAS Number 91541 1 -01 - 7; 0.102 g , 0.630 mmol) in DMF (2.4 ml) and water (0.6 ml) was added K2C03 (0.238 g, 1 .7 mmol) at rt. The reaction mixture was degassed for 30 minutes before addition of PdCI2(dppf) (0.021 g , 0.028 mmol) and heated at 90C for 16 h. The reaction mixture was cooled to rt and quickly poured into saturated aqueous NaHC03 solution (50 ml) and extracted into EtOAc (3 x 20 ml). The combined organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (100% EtOAc) to yield 5-(1 H-indazol-7-yl)pyrazin-2-amine (0.210 g, 0.995 mmol ). LCMS: Method C, 1 .437 min, MS: ES+ 212.18

Reference： [1]Patent: WO2018/65768,2018,A1 .Location in patent: Page/Page column 140

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 59489-71-3 ] {[proInfo.proName]}

Quality Control of [ 59489-71-3 ]

Related Doc. of [ 59489-71-3 ]

Product Details of [ 59489-71-3 ]

Calculated chemistry of [ 59489-71-3 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 59489-71-3 ]

Application In Synthesis of [ 59489-71-3 ]

[ 59489-71-3 ] Synthesis Path-Upstream 1~1

[ 59489-71-3 ] Synthesis Path-Downstream 1~7

Technical Information

Related Functional Groups of [ 59489-71-3 ]

Bromides

Amines

Related Parent Nucleus of [ 59489-71-3 ]

Pyrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 59489-71-3 ]

Related Parent Nucleus of
[ 59489-71-3 ]