[ CAS No. 168123-82-8 ] {[proInfo.proName]}

Name: 168123-82-8|7-Bromopyrido[2,3-b]pyrazine-2,3(1H,4H)-dione|95%
Brand: Ambeed
SKU: A144754
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Quality Control of [ 168123-82-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 168123-82-8 ]

CAS No. :	168123-82-8	MDL No. :	MFCD00460131
Formula :	C₇H₄BrN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SMQUNTGAPNGDHP-UHFFFAOYSA-N
M.W :	242.03	Pubchem ID :	727370
Synonyms :

Calculated chemistry of [ 168123-82-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.68
TPSA :	78.61 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.85
Log Po/w (XLOGP3) :	0.4
Log Po/w (WLOGP) :	0.37
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	0.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.67 mg/ml ; 0.00689 mol/l
Class :	Soluble
Log S (Ali) :	-1.62
Solubility :	5.84 mg/ml ; 0.0241 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.63
Solubility :	0.0569 mg/ml ; 0.000235 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.07

Safety of [ 168123-82-8 ]

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 [ 168123-82-8 ]

* 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 [ 168123-82-8 ]
Downstream synthetic route of [ 168123-82-8 ]

[ 168123-82-8 ] Synthesis Path-Upstream 1~3

1
[ 38875-53-5 ]
[ 95-92-1 ]
[ 168123-82-8 ]

Yield	Reaction Conditions	Operation in experiment
620 mg	for 4 h; Reflux	General procedure: A mixture of 2,3-diaminopyridine in diethyl oxalate (10 mL/1 mmol phenyldiamine) was heated to reflux for 4 h before cooled to room temperature. The resulted solid was filtered,washed with ethyl acetate and 95percent ethanol, decolorized with activated charcoal and recrystallized in water and DMF or DMSO to give 5-azaquinoxalinediones as white solid. 5.2.2.15 7-Bromo-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (15) The title compound was prepared from 2-amino-5-bromopyridine according to the general procedure as white solid (620 mg, 25.6percent). IR (KBr) ν 3199, 3138, 3045, 2751, 1715, 1603, 1446, 1389 cm^-1; ¹H NMR (400 MHz, DMSO-d₆) δ 7.55 (1H, d, J = 1.6 Hz, H-6), 8.15 (1H, d, J = 1.6 Hz, H-8); ¹³C NMR (100 MHz, DMSO-d₆) δ 112.36, 123.20, 123.80, 138.46, 141.83, 154.55, 155.58; HRMS-EI C₇H₄BrN₃O₂ calcd [M+H]⁺ 241.9565, found 241.9567.

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 19 - 32
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 308 - 317
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2949 - 2961

2
[ 38875-53-5 ]
[ 144-62-7 ]
[ 168123-82-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686

3
[ 6945-68-2 ]
[ 168123-82-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686

[ 168123-82-8 ] Synthesis Path-Downstream 1~24

1
[ 38875-53-5 ]
[ 144-62-7 ]
[ 168123-82-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3679 - 3686

2
[ 168123-82-8 ]
7-Bromo-5-oxy-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3679 - 3686

3
[ 6945-68-2 ]
[ 168123-82-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3679 - 3686

Yield	Reaction Conditions	Operation in experiment
536 mg (83%)		8-Aza-6-bromo-1,4-dihydroquinoxaline-2,3-dione (42) A solution of 40 (500 mg, 2.66 mmol) and oxalic acid (760 mg, 4.0 mmol) in 2N aq HCl (3.0 mL) was refluxed for 2 h, then cooled to room temperature. The precipitate was filtered, washed with H2 O (2*2 mL), and dried to give 536 mg (83%) of 42 as a green-yellow powder, mp >370 C. 1 H NMR (DMSO-d6) delta7.548 (s, 1H), 8.160 (s, 1H), 12.011 (s, 1H), 12.461 (s, 1H).

5
[ 38875-53-5 ]
[ 95-92-1 ]
[ 168123-82-8 ]

Yield	Reaction Conditions	Operation in experiment
620 mg	for 4.0h;Reflux;	General procedure: A mixture of 2,3-diaminopyridine in diethyl oxalate (10 mL/1 mmol phenyldiamine) was heated to reflux for 4 h before cooled to room temperature. The resulted solid was filtered,washed with ethyl acetate and 95% ethanol, decolorized with activated charcoal and recrystallized in water and DMF or DMSO to give 5-azaquinoxalinediones as white solid. 5.2.2.15 7-Bromo-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (15) The title compound was prepared from 2-amino-5-bromopyridine according to the general procedure as white solid (620 mg, 25.6%). IR (KBr) nu 3199, 3138, 3045, 2751, 1715, 1603, 1446, 1389 cm-1; 1H NMR (400 MHz, DMSO-d6) delta 7.55 (1H, d, J = 1.6 Hz, H-6), 8.15 (1H, d, J = 1.6 Hz, H-8); 13C NMR (100 MHz, DMSO-d6) delta 112.36, 123.20, 123.80, 138.46, 141.83, 154.55, 155.58; HRMS-EI C7H4BrN3O2 calcd [M+H]+ 241.9565, found 241.9567.
	at 100℃; for 12.0h;	General procedure: A mixture of substituted pyridine-2,3-diamine 1 (20 mmol) anddiethyl oxalate(10 mL) was stirred at 100 C for 12 h and cooled toroom temperature subsequently. Ethoxyethane was added toobtain solid. The formed solid was then centrifuged and dried toobtain brown solid compound of pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione 2. The mixture of pyrido[2,3-b]pyrazine-2,3(1H, 4H)-dione and POCl3(20 ml) was stirred at 130 C and then cooled toroom temperature. The mixture was poured into the ice water. Theformed solid was filter and then evaporated solvent in vacuo toobtain unpurified 2,3-dichloropyrido[2,3-b]pyrazine 3. Then theunpurified was mixture with LiOH (10 mmol) in THF/H2O (5:2,35 mL). The mixture was stirred at 65 C for 12 h. The resultingmixture was cooled to room temperature, and then brine (10 mL)was added to mixture. After extraction with THF (3 50 ml), thecombined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4, and filtered, followed by evaporation of thesolvent in vacuo to obtain the unpurified 2-chloropyrido[2,3-b]pyrazin-3(4H)-one 4a-c. The crude products were purified by columnchromatography on silica gel using petroleum ether/EtOAc(3:1) as eluent to provide the desired product 2-chloropyrido[2,3-b]pyrazin-3(4H)-one derivatives4a-c.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 117,p. 19 - 32
[2]European Journal of Medicinal Chemistry,2016,vol. 121,p. 308 - 317
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 2949 - 2961

6
[ 168123-82-8 ]
(E)-2-(7-bromo-2-(4-hydroxystyryl)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)acetic acid [ No CAS ]