[ CAS No. 120984-76-1 ] {[proInfo.proName]}

Name: 120984-76-1|2-Bromo-3-methylpyrazine|95%
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3d Animation Molecule Structure of 120984-76-1

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Quality Control of [ 120984-76-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 120984-76-1 ]

SDS Specification

Alternatived Products of [ 120984-76-1 ]

Product Details of [ 120984-76-1 ]

CAS No. :	120984-76-1	MDL No. :	MFCD08705769
Formula :	C₅H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NDBBGCAETKIKIC-UHFFFAOYSA-N
M.W :	173.01	Pubchem ID :	12457513
Synonyms :

Calculated chemistry of [ 120984-76-1 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.7
TPSA :	25.78 Å²

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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	1.21
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.31
Log Po/w (SILICOS-IT) :	2.08
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	1.02 mg/ml ; 0.00589 mol/l
Class :	Soluble
Log S (Ali) :	-1.35
Solubility :	7.76 mg/ml ; 0.0449 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.224 mg/ml ; 0.0013 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 120984-76-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 120984-76-1 ]

* 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 [ 120984-76-1 ]
Downstream synthetic route of [ 120984-76-1 ]

[ 120984-76-1 ] Synthesis Path-Upstream 1~1

1
[ 19838-07-4 ]
[ 120984-76-1 ]

Reference： [1] Journal of the American Chemical Society, 1956, vol. 78, p. 2141,2144

[ 120984-76-1 ] Synthesis Path-Downstream 1~11

1
[ 19838-07-4 ]
[ 120984-76-1 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 2141,2144

2
[ 120984-76-1 ]
CuCN [ No CAS ]
[ 65735-15-1 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 2141,2144

3
[ 120984-76-1 ]
[ 104893-52-9 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 2141,2144

4
[ 120984-76-1 ]
cis-4-amino-N-[1-(2-aminoethyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide [ No CAS ]
[ 67-66-3 ]
cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[2-[(3-methyl-2-pyrazinyl)amino]ethyl]-4-piperidinyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.95 parts (36%)	With ammonium hydroxide; potassium iodide; In methanol; dichloromethane;	EXAMPLE 10 A mixture of 8.56 parts of <strong>[120984-76-1]2-bromo-3-methylpyrazine</strong> and 0.1 parts of potassium iodide was pulverized and 2 parts of cis-4-amino-N-[1-(2-aminoethyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide were added. The whole was stirred for 3 hours at 120 C. The reaction mixture was taken up in dichloromethane and water and made alkaline with ammonium hydroxide. The organic layer was separated, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The first fractions was collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.95 parts (36%) of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[2-[(3-methyl-2-pyrazinyl)amino]ethyl]-4-piperidinyl]benzamide; mp. 169.5 C. (compound 27).

Reference： [1]Patent: US4906643,1990,A

5
[ 120984-76-1 ]
[ 1609581-41-0 ]

Reference： [1]Patent: WO2014/72881,2014,A1

6
[ 120984-76-1 ]
[ 1609578-47-3 ]

Reference： [1]Patent: WO2014/72881,2014,A1

7
[ 120984-76-1 ]
[ 1609581-05-6 ]
[ 1609577-13-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 130.0℃; for 1.0h;Microwave irradiation;	2-Bromo-3-methylpyrazine (104 mg, 0.600 mmol),tetrakis(triphenylphosphine)palladium(0) (95%, 133 mg, 0.109 mmol) and sodium carbonate(175 mg, 1.64 mmol) were combined with 4-[3-methoxy-4-(4,4,5,5-tetramethyl-1 3,2-dioxaborolan-2-yl)phenoxy]furo[3 ,2-c]pyridine [Cl 0, which was prepared in analogous fashion to4-[3-methyl-4-(4 ,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2-yl)phenoxy]furo[3,2-c]pyrid me (C2) inExample 1] (200 mg, 0.545 mmol) in 1,4-dioxane (3 mL) and water (1 mL). The reaction mixturewas heated to 13000 in a microwave reactor for 1 hour. The mixture was cooled to roomtemperature, and the supernatant was decanted into another flask. The remaining solids were washed with ethyl acetate (3 x 10 mL) and the combined organic portions were concentrated in vacuo. Purification was carried out twice using silica gel chromatography (First column: Eluent:2% methanol in dichloromethane; Second column: Gradient: 0% to 100% ethyl acetate inheptane). The colorless fractions were combined and concentrated under reduced pressure to provide the product as a white solid. Yield: 85 mg, 0.25 mmol, 46%. LCMS m/z 334.0 (M+H). 1H NMR (400 MHz, CDCl3) oe 8.47 (AB quartet, downfield doublet is broadened, JAB=2.S Hz, AVAB=l4 Hz, 2H), 8.08 (d, J=5.9 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.36 (d, J8.0 Hz, 1H), 7.25- 7.28 (m, 1H, assumed; partially obscured by solvent peak), 6.90-6.96 (m, 2H), 6.88 (dd, J=2.2,0.8 Hz, 1H), 3.79 (s, 3H), 2.50 (s, 3H). Yellow fractions were repurified to provide additional product: 55 mg, overall yield: 75%.

Reference： [1]Patent: WO2014/72881,2014,A1 .Location in patent: Page/Page column 80

8
[ 120984-76-1 ]
C₂₁H₂₄BNO₄ [ No CAS ]
[ 1609578-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120.0℃; for 5.0h;Microwave irradiation; Inert atmosphere;	4-[3-Methyl-4-(4,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2-yl)phenoxy]furo[3 ,2-c]pyridine (C2) (250 mg, 0.712 mmol), 5-bromo-4,6-dimethylpyrimidine (160 mg, 0.855 mmcl), tris(dibenzylideneacetone)dipalladium(0) (95%, 26.9 mg, 0.142 mmol), tricyclohexyiphosphine (79.9 mg, 0.285 mmcl) and potassium phosphate (302 mg, 1.42 mmol) were combined in a 3:1mixture of 1 ,4-dioxane and water (12 mL), and subjected to irradiation in a microwave reactor at120 00 for 5 hours. The reaction mixture was filtered through Celite; the filtrate was concentrated under reduced pressure, taken up in ethyl acetate, filtered through silica gel (1 g), and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 123 mg, 0.371 mmol,52%. LCMS m/z 332.1 (M+H). 1H NMR (500 MHz, ODd3) oe 8.98 (s, 1H), 8.07 (d, J5.9 Hz, 1H),7.67 (d, J=2.2 Hz, 1H), 7.25-7.27 (m, 1H, assumed; partially obscured by solvent peak), 7.24(br d, J=2.4 Hz, 1H), 7.19 (brdd, J=8.3, 2.4 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.90 (dd, J=2.2, 1.0 Hz, 1H), 2.27 (s, 6H), 2.04 (s, 3H).

Reference： [1]Patent: WO2014/72881,2014,A1 .Location in patent: Page/Page column 75; 135

9
[ 120984-76-1 ]
[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy][tri(propan-2-yl)]silane [ No CAS ]
2-(2-methoxy-4-[tri(propan-2-yl)silyl]oxy}phenyl)-3-methylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100.0℃; for 2.0h;	A solution of C39 (2.35 g, 5.78 mmol), <strong>[120984-76-1]2-bromo-3-methylpyrazine</strong> (1.0 g, 5.8mmol), [1 ,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (634 mg, 0.866mmol), and potassium carbonate (3.2 g, 23 mmol) in a mixture of 1,4-dioxane (30 mL) and water (8 mL) was stirred at 100 C for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (Eluent: ethyl acetate) to afford the product as a yellow solid. Yield:0.90 g, 2.4 mmol, 42%. 1H NMR (400 MHz, CDCI3) oe 8.46(brd, J=2 Hz, 1H), 8.41 (d, J=2.6 Hz, 1H), 7.15 (d, J=8.2 Hz, 1H), 6.60 (dd, J=8.3, 2.3 Hz, 1H), 6.54 (d, J=2.3 Hz, 1H), 3.76 (5, 3H), 2.43 (5, 3H), 1.24-1.37 (m, 3H), 1.08-1.18 (m, 18H).

Reference： [1]Patent: WO2015/162515,2015,A1 .Location in patent: Page/Page column 146; 147

10
[ 120984-76-1 ]
3-methoxy-4-(3-methylpyrazin-2-yl)phenol [ No CAS ]

Reference： [1]Patent: WO2015/162515,2015,A1

11
[ 120984-76-1 ]
7-[3-methoxy-4-(3-methylpyrazin-2-yl)phenoxy]thieno[2,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2015/162515,2015,A1

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[ 120984-76-1 ]

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H261	In contact with water releases flammable gas
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H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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

[ CAS No. 120984-76-1 ] {[proInfo.proName]}

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Calculated chemistry of [ 120984-76-1 ]

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Application In Synthesis of [ 120984-76-1 ]

[ 120984-76-1 ] Synthesis Path-Upstream 1~1

[ 120984-76-1 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 120984-76-1 ]

Bromides

Related Parent Nucleus of [ 120984-76-1 ]

Pyrazines

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Prevention

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Related Functional Groups of
[ 120984-76-1 ]

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[ 120984-76-1 ]