[ CAS No. 74290-67-8 ] {[proInfo.proName]}

Name: 74290-67-8|2-Amino-5-bromo-3-methylpyrazine|98%
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SKU: A163949
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Quality Control of [ 74290-67-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 74290-67-8 ]

Product Details of [ 74290-67-8 ]

CAS No. :	74290-67-8	MDL No. :	MFCD08705773
Formula :	C₅H₆BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VZZCBPAGRWGQDG-UHFFFAOYSA-N
M.W :	188.03	Pubchem ID :	21785147
Synonyms :

Calculated chemistry of [ 74290-67-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.1
TPSA :	51.8 Å²

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) :	1.39
Log Po/w (XLOGP3) :	0.86
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	0.11
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	0.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.04
Solubility :	1.71 mg/ml ; 0.0091 mol/l
Class :	Soluble
Log S (Ali) :	-1.53
Solubility :	5.53 mg/ml ; 0.0294 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.549 mg/ml ; 0.00292 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 74290-67-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 74290-67-8 ]

* 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 [ 74290-67-8 ]
Downstream synthetic route of [ 74290-67-8 ]

[ 74290-67-8 ] Synthesis Path-Upstream 1~2

1
[ 74290-67-8 ]
[ 19838-08-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147

2
[ 19838-08-5 ]
[ 74290-67-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With pyridine; bromine In chloroform; water	(iii) A solution of bromine (0.26 ml) in chloroform (40 ml) was added dropwise to a stirred solution of 2-amino-3-methylpyrazine (0.453 g) and pyridine (0.4 ml) in chloroform (100 ml) with shielding from sunlight, over a period of 1 hour. The reaction mixture was stirred for a further 30 minutes and then water (25 ml) was added. The organic layer was separated, dried (MgSO₄) and evaporated to afford a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane, to give 2-amino-5-bromo-3-methylpyrazine as a white solid (0.312 g, 28percent), m.p. 51°-52° C.; mass spectrum (+ve CI): 188 (M+H)⁺.

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
[2] Patent: US5861401, 1999, A,

[ 74290-67-8 ] Synthesis Path-Downstream 1~29

1
[ 74290-67-8 ]
[ 19838-08-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 143 - 147

2
[ 19838-08-5 ]
[ 74290-67-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With pyridine; bromine; In chloroform; water;	(iii) A solution of bromine (0.26 ml) in chloroform (40 ml) was added dropwise to a stirred solution of 2-amino-3-methylpyrazine (0.453 g) and pyridine (0.4 ml) in chloroform (100 ml) with shielding from sunlight, over a period of 1 hour. The reaction mixture was stirred for a further 30 minutes and then water (25 ml) was added. The organic layer was separated, dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane, to give 2-amino-5-bromo-3-methylpyrazine as a white solid (0.312 g, 28%), m.p. 51-52 C.; mass spectrum (+ve CI): 188 (M+H)+.

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 143 - 147
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6342 - 6345
[3]Patent: US5861401,1999,A

3
[ 605-65-2 ]
[ 74290-67-8 ]
5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 996 - 1004

4
[ 605-65-2 ]
[ 74290-67-8 ]
[ 77-92-9 ]
5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane; mineral oil;	EXAMPLE 11 Sodium hydride (60% dispersion in mineral oil; 0.1 g) was added portionwise to a stirred solution of <strong>[74290-67-8]2-amino-5-bromo-3-methylpyrazine</strong> (0.188 g) in 1,2-dimethoxyethane (DHE; 4 ml). After 5 minutes 5-dimethylamino-1-naphthalenesulphonyl chloride (0.3 g) was added, in a single portion, and the reaction was allowed to a stir for 18 hours. 2M Aqueous citric acid solution (10 ml) was added and the reaction was extracted with dichloromethane (3*25 ml). The combined extracts were dried (MgSO4) and evaporated to give a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane/diethyl ether (1:1) to give 5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide as a cream solid (0.138 g, 33%), m.p. 171-172 C.; mass spectrum (+ve FAB, DMSO/methanol/NBA): 421 (M+H)+.

Reference： [1]Patent: US5861401,1999,A

5
[ 1360552-40-4 ]
[ 74290-67-8 ]
[ 1360550-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 120.0℃; for 1.0h;Microwave irradiation;	To a solution of I-69 (300 mg, 0.6 mmol) in DMF (10 mL) are added I-87 (140 mg, 0.7 mmol), tetrakis(triphenylphosphine)palladium (0) (70 mg, 0.06 mmol) and 2M Na2CO3 (1.5 mL, 3.0 mmol). The mixture is heated to 100 C. for 1 hour in a microwave reactor. The mixture is cooled down and is extracted with H2O (20 mL) and EtOAc (30 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (200 mg). Example 176-180, Table 1-the reaction is run at 120 C.Example 176-180, Table 1-the reaction is run at 120 C. [0509] Example 184-185, Table 1-the reaction is run at 120 C

Reference： [1]Patent: US2013/195879,2013,A1 .Location in patent: Paragraph 0504; 0505; 0506; 0510; 0600

6
[ 1527525-39-8 ]
[ 74290-67-8 ]
[ 1527525-40-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In dichloromethane; N,N-dimethyl acetamide; at 150.0℃; for 0.75h;Inert atmosphere; Microwave irradiation;	A mixture of tert-butyl 4-[6-(6-tributylstannylpyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-1,4-diazepane-1-carboxylate (0.5852 mmol; 400 mg), 5-bromo-3-methyl-pyrazin-2-amine (1.170 mmol; 220.1 mg), tricyclohexylphosphine (0.1405 mmol; 39.39 mg) and tris(dibenzylideneacetone)dipalladium (0) (0.05 852 mmol; 53.59 mg) in N,N-Dimethylacetamide (30 mL) was purged with Argon for 1 min. The reaction mixture was sealedin a Biotage microwave tube and heated under microwave at 150C for 45 min. The mixture was partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 10% MeOH in DCM to afford tert-butyl 4-[6-[6-(5-amino-6-methyl-pyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate (115.0 mg, 39%).

Reference： [1]Patent: WO2014/1377,2014,A1 .Location in patent: Page/Page column 142

7
[ 74290-67-8 ]
[ 1616415-86-1 ]

Reference： [1]Patent: WO2014/96423,2014,A1

8
[ 74290-67-8 ]
[ 1616415-87-2 ]

Reference： [1]Patent: WO2014/96423,2014,A1

9
[ 74290-67-8 ]
[ 1616415-88-3 ]

Reference： [1]Patent: WO2014/96423,2014,A1

10
[ 74290-67-8 ]
[ 1616415-89-4 ]

Reference： [1]Patent: WO2014/96423,2014,A1

11
[ 24424-99-5 ]
[ 74290-67-8 ]
[ 1616416-09-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[74290-67-8]2-amino-5-bromo-3-methylpyrazine</strong> (46.5 g, 247.3 mmol) in acetonitrile (450 mL) and THF (750 mL) was added DMAP (3 g, 24.7 mmol). The reaction mixture was stirred for 15 minutes before the addition of di-tert-butyl dicarbonate (242 g, 1 112.8 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated in vacuo, then diluted with EtOAc (750 mL) and washed with water (500 mL). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The black tar was purified via flash chromatography, using a 10-15% EtOAc in heptane gradient. The resultant solid was triturated with IP A. The resulting white solid (the bis-tert-butoxycarbonyl derivative) was dissolved in methanol (3000 mL), then K2CO3 (61.25 g, 443 mmol) was added. The reaction mixture was stirred overnight at room temperature, then at 60C for 1 h, then allowed to cool and concentrated in vacuo. The residue was dissolved in DCM (1000 mL), then washed with water (2 x 1000 mL) and brine (500 mL). The organic layers were dried over magnesium sulphate, then concentrated in vacuo, to give the title compound (38 g, 80% pure by LCMS). LCMS (ES+) [M+H]+ 288.1 and 289.1 , RT 1.42 minutes (method 1).

Reference： [1]Patent: WO2014/96423,2014,A1 .Location in patent: Page/Page column 66

12
[ 74290-67-8 ]
N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-fluoro-4-[(3R)-3-methylpiperazin-1-yl]benzamide [ No CAS ]

Reference： [1]Patent: WO2015/197503,2015,A1

13
[ 74290-67-8 ]
(R)-tert-butyl 4-(4-(2,8-dimethylimidazo[1,2-a]pyrazin-6-ylcarbamoyl)-3-fluorophenyl)-2-methylpiperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/197503,2015,A1

14
[ 126-38-5 ]
[ 74290-67-8 ]
6-bromo-2,8-dimethylimidazo[1,2-a]pyrazine [ No CAS ]