[ CAS No. 122450-96-8 ] {[proInfo.proName]}

Name: 122450-96-8|7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one|95%
Brand: Ambeed
SKU: A196227
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Quality Control of [ 122450-96-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 122450-96-8 ]

CAS No. :	122450-96-8	MDL No. :	MFCD09834134
Formula :	C₇H₅BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ATRMUPKQFDRURR-UHFFFAOYSA-N
M.W :	229.03	Pubchem ID :	15925983
Synonyms :

Calculated chemistry of [ 122450-96-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.76
TPSA :	51.22 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) :	-7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.67
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	0.6
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.7
Consensus Log Po/w :	1.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	1.61 mg/ml ; 0.00703 mol/l
Class :	Soluble
Log S (Ali) :	-1.49
Solubility :	7.44 mg/ml ; 0.0325 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.12
Solubility :	0.175 mg/ml ; 0.000766 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.29

Safety of [ 122450-96-8 ]

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 [ 122450-96-8 ]

* 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 [ 122450-96-8 ]
Downstream synthetic route of [ 122450-96-8 ]

[ 122450-96-8 ] Synthesis Path-Upstream 1~2

1
[ 20348-09-8 ]
[ 122450-96-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine In N,N-dimethyl-formamide at 20℃;	To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76percent yield). IH NMR <n="95"/>(DMSO-d6) δ (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).
69%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 72 h;	a) 7-Bromo-2H-pyrido[3,2-jb][1 ,4]oxazin-3(4H)-oneA mixture of 2H-pyrido[3,2-d][1 ,4]oxazin-3(4H)-one (1.30 g, 8.66 mmol) and N-bromosuccinimide (1.70 g, 9.53 mmol) in DMF (30 mL) was stirred for three days at room temperature . Water (10 mL) was added and the suspension was cooled EPO <DP n="58"/>with an ice bath. The resulting precipitate was filtered, washed with water, and air- dried in a Buchner funnel to give the title compound (1.37 g, 69percent) as a white solid.MS(ES+) m/e 229 [M+H]+.
260 mg	With bromine In N,N-dimethyl-formamide at 20℃; for 2 h;	the step A compound (3.24mmol) was dissolved in 14 ml of N, N- dimethylformamide, then slowly added Bromine(3.56 mmol). At room temperature it wasstirred for 2 hours then water (300 ml) wasadded .the resulting precipitate was collected by filtration then it was washed with water and dried to give 260 mg ofthe title compound.

Reference： [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Patent: WO2009/100536, 2009, A1, . Location in patent: Page/Page column 93-94
[3] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 56-57
[4] Patent: US4906629, 1990, A,
[5] Patent: US4822794, 1989, A,
[6] Patent: US4866074, 1989, A,
[7] Patent: WO2004/14384, 2004, A2, . Location in patent: Page/Page column 256; 262
[8] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0608-0610

2
[ 16867-03-1 ]
[ 122450-96-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Patent: CN103130792, 2016, B,

[ 122450-96-8 ] Synthesis Path-Downstream 1~28

1
[ 20348-09-8 ]
[ 122450-96-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine; In N,N-dimethyl-formamide; at 20℃;	To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76% yield). IH NMR <n="95"/>(DMSO-d6) delta (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).
69%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 72h;	a) 7-Bromo-2H-pyrido[3,2-jb][1 ,4]oxazin-3(4H)-oneA mixture of 2H-pyrido[3,2-d][1 ,4]oxazin-3(4H)-one (1.30 g, 8.66 mmol) and N-bromosuccinimide (1.70 g, 9.53 mmol) in DMF (30 mL) was stirred for three days at room temperature . Water (10 mL) was added and the suspension was cooled EPO <DP n="58"/>with an ice bath. The resulting precipitate was filtered, washed with water, and air- dried in a Buchner funnel to give the title compound (1.37 g, 69%) as a white solid.MS(ES+) m/e 229 [M+H]+.
	With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;	Step 1. 7-Bromo-2H-pyrido[3,2-b]1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and the mixture is chilled The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried under vacuum at 70 C. and then used directly in the next step.

	With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;	Step 1. 7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and chilled. The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried in a vac oven at 70 C. and then used directly in the next step.
	With N-Bromosuccinimide; In water; N,N-dimethyl-formamide;	Step 1. 7-Bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one To a solution of 5.6 g <strong>[20348-09-8]2H-pyrido[3,2-b]-1,4-oxazin-3-(4H)-one</strong> dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and chilled. The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried in a vac oven at 70 C. and then used directly in the next step.
	With bromine; In DMF (N,N-dimethyl-formamide);	In Scheme 90c, the oxazine (24) can be prepared from compound (22) using a similar strategy previously used for (21). Base catalyzed addition of (22) to [CHLOROACETIC] acid followed by cyclization affords intermediate (22). Compound (22) can undergo halogenation using bromine in an aprotic solvent such as DMF to give compound (24).
260 mg	With bromine; In N,N-dimethyl-formamide; at 20℃; for 2h;	the step A compound (3.24mmol) was dissolved in 14 ml of N, N- dimethylformamide, then slowly added Bromine(3.56 mmol). At room temperature it wasstirred for 2 hours then water (300 ml) wasadded .the resulting precipitate was collected by filtration then it was washed with water and dried to give 260 mg ofthe title compound.
65.30 g	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 50℃; for 20h;	To 2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one (45.0 g, 300 mmol) in DMF (360 mL) at 20 C was added NBS (74.7 g, 420 mmol) in one portion, and the resulting brownish suspension was heated at 50 C for 20 hours. The mixture was cooled to 25 C, and the content was poured into stirred water (1 L) in a 3 L flask fitted with an overhead mechanical stirrer. The resulting aqueous suspension was stirred at room temperature for 30 minutes followed by filtration. The yellowish cake was washed with 10% Na2S203 solution (100 mL) followed by water (2 x 100 mL). The cake was aspirated at room temperature under house vacuum overnight. The solids were washed with Et20 (100 mL), aspirated under house vacuum at room temperature for 18 hours, and then dried under high vacuum at 50 C for 72 hours to afford the title compound (65.30 g) as a light tan-colored powdery solid. LC-MS (ES) m/z = 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 4.68 (s, 2H), 7.66 (d, J = 2.0 Hz, 1 H), 8.02 (d, J = 2.0 Hz, 1 H), 1 1 .44 (br. s., 1 H).

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 133 - 142
[2]Patent: WO2009/100536,2009,A1 .Location in patent: Page/Page column 93-94
[3]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 56-57
[4]Patent: US4906629,1990,A
[5]Patent: US4822794,1989,A
[6]Patent: US4866074,1989,A
[7]Patent: WO2004/14384,2004,A2 .Location in patent: Page/Page column 256; 262
[8]Patent: CN103130792,2016,B .Location in patent: Paragraph 0608-0610
[9]Patent: WO2019/49061,2019,A1 .Location in patent: Page/Page column 175

2
[ 122450-96-8 ]
[ 74-88-4 ]
[ 122450-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In tetrahydrofuran; at 50℃;	To a mixture of <strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one</strong> (Ark Pharma, cat No.AK-30821: 204 mg, 0.893 mmol) and cesium carbonate (440 mg, 1.3 mmol) in tetrahydrofuran (3 mL) was added methyl iodide (2.0 mL, 30 mmol). The mixture was stirred at 50 C. overnight. After cooling to room temperature, the reaction mixture was filtered and concentrated. The residue was used in the next step without further purification. LC-MS calculated for C8H8BrN2O2 (M+H)+: m/z=243.0. found 242.9.
	With caesium carbonate; In tetrahydrofuran; at 50℃;	To a mixture of <strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one</strong> (Ark Pharma, cat AK-30821: 204 mg, 0.893 mmol) and cesium carbonate (440 mg, 1.3 mmol) in tetrahydrofuran (3 mL) was added methyl iodide (2.0 mL, 30 mmol). The mixture was stirred at 50 C. overnight. After cooling to room temperature, the reaction mixture was filtered and concentrated. The residue was used in the next step without further purification. LC-MS calculated for C8H8BrN2O2 (M+H)+: m/z=243.0. found 242.9.

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 133 - 142
[2]Patent: US2016/9720,2016,A1 .Location in patent: Paragraph 0625
[3]Patent: US2016/9712,2016,A1 .Location in patent: Paragraph 0614

3
[ 16867-03-1 ]
[ 122450-96-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 133 - 142
[2]Patent: CN103130792,2016,B

4
[ 122450-96-8 ]
7-Acetyl-4-methyl-4H-pyrido[3,2-b][1,4]oxazin-3-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 133 - 142

5
[ 128796-39-4 ]
[ 122450-96-8 ]
7-[4-(trifluoromethyl)phenyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃; for 18h;	b) 7-[4-(Trifluoromethyl)phenyl]-2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one A mixture of 7-bromo-2H-pyrido[3,2-][1 ,4]oxazin-3(4H)-one (0.401 g, 1.75 mmol), 4-(trifluoromethyl)benzeneboronic acid (0.497 g, 2.63 mmol), tetrakis(triphenylphosphine) palladium (0) (0.202 g, 0.175 mmol), and 2M aqueous potassium carbonate (4.8 ml_, 9.63 mmol) in DMF (11 mL) was heated for 18 hours at 1000C. The reaction was cooled and filtered through Celite. The filtrate was diluted with ethyl acetate, washed with water and saturated sodium chloride, dried (Na2SC>4), concentrated in vacuo, and purified by flash chromatography on silica gel(2%-3% MeOH: CH2CI2) to give the title compound (0.032 g, 6 %) as a white cotton- like solid. MS(ES+) m/e 295 [MH-H]+.

Reference： [1]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 57

6
[ 77-78-1 ]
[ 122450-96-8 ]
[ 122450-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Step 2. 4-methyl-<strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one</strong> To a suspension of 5 g of <strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one</strong> (0.022 mole) in 90 ml of THF is added 24 ml of LiN(TMS)2 (0.024 mole) in THF. The homogenous solution is maintained under nitrogen at room temperature for 20 min., 3.03 g (0.024 mole) of dimethylsulfate is added and the reaction mixture allowed to stir overnight. The reaction mixture is then quenched with 20 ml of sat. ammonium chloride and extracted with 380 ml ethyl acetate. The ethyl acetate is then washed with 330 ml sat. ammonium chloride, dried over sodium sulfate and concentrated to obtain off white product which is used directly in the next step.
	In tetrahydrofuran;	Step 2. 4-Methyl-<strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one</strong> To a suspension of 5 g of <strong>[122450-96-8]7-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one</strong> (0.022 mole) in 90 ml of THF is added 24 ml of LiN(TMS)2 (0.024 mole) in THF. The homogenous solution is maintained under nitrogen at room temperature for 20 min., 3.03 g (0.024 mole) of dimethylsulfate is added and the reaction mixture allowed to stir overnight. The reaction mixture is then quenched with 20 ml of sat. ammonium chloride and extracted with 380 ml ethyl acetate. The ethyl acetate is then washed with 330 ml sat. ammonium chloride, dried over sodium sulfate and concentrated to obtain off white product which is used directly in the next step.

Reference： [1]Patent: US4822794,1989,A
[2]Patent: US4866074,1989,A

7
[ 329-01-1 ]
[ 122450-96-8 ]
1-(4-ethynylphenyl)-3-(3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In pyridine; at 0 - 20℃; for 2h;	A solution of aniline 1 (200 mul, 1.912 mmol) in pyridine (1.5 mL), was stirred at OoC under N2, and treated with neat isocyanate 12 (292 mul, 2.084 mmol). The reaction mixture was stirred at the OoC for 30 minutes, then at room temperature for 1.5 hours. The mixture was quenched with saturated ammonium chloride, stirred for 30 minutes and extracted with DCM. The organic phase was washed with ammonium chloride, dried, filtered and concentrated. The residue was triturated with DCM to afford title compound 17 (530 mg, 91% yield). IH NMR (DMSO-d6) delta (ppm): 9.11 (s, IH), 8.92 (s, IH), 8.00 (s, IH), 7.67 (t, J = 1.8 Hz, IH), 7.61-7.49 (m, 2H), 7.42 (ddd, J = 8.2, 2.2, 1.2 Hz, IH), 7.34-7.28 (m, 2H), 7.10 (dt, J = 7.5, 1.3 Hz, IH), 4.15 (s, IH).

Reference： [1]Patent: WO2009/100536,2009,A1 .Location in patent: Page/Page column 93; 94

8
1-(4-ethynylphenyl)-3-(3-(trifluoromethyl)phenyl)urea [ No CAS ]
[ 122450-96-8 ]
[ 1181621-12-4 ]

Yield	Reaction Conditions	Operation in experiment
16%	With copper(l) iodide; triethylamine;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 70℃; for 4h;Inert atmosphere;	Compound 17 (319 mg, 1.05 mmol), compound 20 (200 mg, 0.87 mmol), copper iodide(83 mg, 0.44 mmol) and tetrakis(triphenylphosphine)palladium (151 mg, 0.13 mmol) were suspended in triethylamine (2 mL, 14.35 mmol) and acetonitrile (8 mL) and the mixture was put under argon (air evacuated by vacuum). The flask with the reaction mixture was heated at 70oC for 4 hours. The mixture was partitioned between aqueous saturated NH4C1 solution and DCM. A precipitate was formed in DCM which was collected by filtration, washed with NH4C1 saturated solution. This material was then suspended in water, sonicated and then stirred overnight. The solid was collected by filtration, dried then sonicated again in DCM and collected by filtration to afford title compound 18 (65 mg, 16% yield). IH NMR (DMSO-d6) delta (ppm): 9.41 (s, IH), 9.23 (s, IH), 8.21 (d, IH, J=2.0 Hz), 8.11 (s, IH), 7.88 (s, IH), 7.55-7.7 (m, 3H), 7.4-7.5 (m, 3H), 7.26 (d, IH, J=6.8 Hz), 4.78 (s, 2H). MS (m/z): 453.2 (M+H).

Reference： [1]Patent: WO2009/100536,2009,A1 .Location in patent: Page/Page column 93; 94

9
[ 122450-96-8 ]
[ 1066-54-2 ]
C₁₂H₁₄N₂O₂Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4701 - 4719

10
[ 122450-96-8 ]
[ 1318109-53-3 ]

Reference： [1]Patent: WO2011/22473,2011,A1

11
[ 122450-96-8 ]
[ 1267854-03-4 ]

Reference： [1]Patent: WO2011/22473,2011,A1

12
[ 122450-96-8 ]
[ 1267854-04-5 ]

Reference： [1]Patent: WO2011/22473,2011,A1

13
[ 122450-96-8 ]
[ 1267849-56-8 ]

Reference： [1]Patent: WO2011/22473,2011,A1

14
[ 24424-99-5 ]
[ 122450-96-8 ]
[ 1267854-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃;	7-Bromo-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-one (658 mg,2.86 mmol) was stirred in 10 mL of THF. Di-t-butyl dicarbonate (687 mg, 3.15 mmol) and DMAP (18 mg, 0.15 mmol) were added and the resulting mixture was stirred at rt overnight, whereupon analysis by TLC indicated complete reaction. The mixture was partitioned between EtOAc (20 mL) and brine (15 mL), and the organic layer was dried over MgSC^ and concentrated under reduced pressure to afford tert-butyl 7- bromo-3-oxo-2H-pyrido[3,2-b][l,4]oxazine-4(3H)-carboxylate (900 mg) as a white solid, which was used directly for the next step.

Reference： [1]Patent: WO2011/22473,2011,A1 .Location in patent: Page/Page column 121

15
[ 122450-96-8 ]
4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one [ No CAS ]

Reference： [1]Patent: US2016/9720,2016,A1
[2]Patent: US2016/9712,2016,A1

16
[ 122450-96-8 ]
4-[8-[4-(dimethylamino)piperidin-1-yl]-5-(4-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)imidazo[1,5-a]pyrazin-6-yl]benzonitrile [ No CAS ]

Reference： [1]Patent: US2016/9712,2016,A1

17
[ 122450-96-8 ]
4-ethyl-7-(1-((2-ethyloxazol-4-yl)methyl)-1H-benzo[d]imidazol-2-yl)-3-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine [ No CAS ]