[ CAS No. 105544-30-7 ] {[proInfo.proName]}

Name: 105544-30-7|Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate|98%
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Quality Control of [ 105544-30-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 105544-30-7 ]

CAS No. :	105544-30-7	MDL No. :	MFCD01648643
Formula :	C₉H₉BrN₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UHIILDDDMFTHKM-UHFFFAOYSA-N
M.W :	305.08	Pubchem ID :	4647502
Synonyms :

Calculated chemistry of [ 105544-30-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	6
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.96
TPSA :	94.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	1.96
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	0.28
Log Po/w (SILICOS-IT) :	0.04
Consensus Log Po/w :	1.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.83
Solubility :	0.45 mg/ml ; 0.00147 mol/l
Class :	Soluble
Log S (Ali) :	-3.56
Solubility :	0.0832 mg/ml ; 0.000273 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.411 mg/ml ; 0.00135 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.69

Safety of [ 105544-30-7 ]

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 [ 105544-30-7 ]

* 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 [ 105544-30-7 ]
Downstream synthetic route of [ 105544-30-7 ]

[ 105544-30-7 ] Synthesis Path-Upstream 1~3

1
[ 67443-38-3 ]
[ 623-50-7 ]
[ 105544-30-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1 h;	Method I: 5-bromo-2-chloro-3-nitropyridine (100 mg, 0.42 mmol) and Ethyl glycolate (0.044 mL, 0.46 mmol) were dissolved in THF (5 mL) and cooled to 0°C. Sodium hydride (0.015 mL, 0.46 mmol) was added and the mixture was stirred for 1hr at room temperature. Reaction mixture was poured in ice water and extracted with EtOAc (2 x 10ml). The organiclayer was washed with brine (10ml), dried over sodium sulphate and concentrated. The crude product was purified by flash column using 100-200 silica gel to ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (105 mg, 82 percent) 9(b). ¹H NMR (300 MHz, DMSO-d₆) δ = 1.27 (s, 3H), 4.25 (q, 2 H), 5.12 (s, 2H) 8.40 (d, J = 2.07 Hz, 1 H), 8.47 (d, J = 2.07 Hz, 1 H); ESMS: m/z 306.8 [M+1]
49%	Stage #1: With sodium hydride In 1,4-dioxane at 70℃; for 1 h; Stage #2: at 20 - 70℃; for 17 h;	Step 1. Sodium hydride (55percent dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of ethyl glycolate (1.43 g, 13.8 mmol) in 1,4-dioxane, and the reaction mixture was heated at 70° C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70° C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (Na₂SO₄), and evaporated. Chromatography (SiO₂, hexane-ethyl acetate gradient) furnished (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (1.03 g, 49percent). Light yellow liquid, MS (ISP)=305.1 (M+H)⁺.
44%	Stage #1: With sodium hydride In 1,4-dioxane at 20 - 30℃; for 0.75 h; Stage #2: at 0 - 80℃;	To a suspension of sodium hydride (5.31 g, 133 mmol) in 1 ,4-dioxane (250 ml), ethyl glycolate (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30°C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1 ,4- dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0°C. The resulting reaction mixture was heated to 80°C overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by Biotage silica chromatography (gradient 0percent to 10percent ethyl acetate in n- hexanes) to give the title compound (1 .8g, 44percent). N R (500 MHz, CDCI₃): 8.48 (1 H, s), 8.42 (1 H, s), 5.07 (2H, s), 4.28-4.24 (2H, q), 1.31-1.28 (3H, t).

Reference： [1] Synthetic Communications, 2013, vol. 43, # 24, p. 3315 - 3321
[2] Patent: US2007/191603, 2007, A1, . Location in patent: Page/Page column 37
[3] Patent: WO2011/77098, 2011, A1, . Location in patent: Page/Page column 157-158
[4] Patent: WO2007/77961, 2007, A2, . Location in patent: Page/Page column 358

2
[ 67443-38-3 ]
[ 38233-96-4 ]
[ 105544-30-7 ]

Reference： [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1986, vol. 26, # 3, p. 99

3
[ 105544-30-7 ]
[ 105544-36-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: at 60℃; for 2.5 h; Stage #2: With sodium carbonate In methanol; dichloromethane; water	Step 2. Iron powder (22.8 g, 408 mmol) was added to a solution of (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (2.28 g, 7.47 mmol) in acetic acid (230 mL), and the reaction mixture was heated at 60° C. over 150 min, cooled to room temperature, and filtered. The filtrate was evaporated, taken up in dichloromethane/methanol 1:1 and neutralized with 1 M aq. sodium carbonate solution. The organic layer was washed with water and the aqueous layer re-extracted with dichloromethane. The combined organic layers were washed again with 1 M aq. sodium carbonate solution, dried (Na₂SO₄), and evaporated to produce 7-bromo-1H-4-oxa-1,5-diaza-naphthalen-2-one (1.46 g, 85percent). Off-white solid, MS (ISP)=226.9 (M-H)^-.

Reference： [1] Patent: US2007/191603, 2007, A1, . Location in patent: Page/Page column 37
[2] Zeitschrift fuer Chemie (Stuttgart, Germany), 1986, vol. 26, # 3, p. 99
[3] Patent: WO2007/77961, 2007, A2, . Location in patent: Page/Page column 358
[4] Synthetic Communications, 2013, vol. 43, # 24, p. 3315 - 3321

[ 105544-30-7 ] Synthesis Path-Downstream 1~62

1
[ 67443-38-3 ]
[ 38233-96-4 ]
[ 105544-30-7 ]

Reference： [1]Zeitschrift fur Chemie,1986,vol. 26,p. 99

2
[ 105544-30-7 ]
[ 130751-80-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1990,vol. 332,p. 265 - 268

3
[ 105544-30-7 ]
[ 105544-36-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iron; acetic acid; at 70℃;	To a solution of B1-1 (5.0 g, 16 mmol) in acetic acid (80 mL) was added slowly Fe (5.5 g, 98 mmol) at 70 C. The mixture was stirred at 70 C for 3 h. After cooling to room temperature, the mixture was filtered and evaporated to remove most of acetic acid. The residue was poured into iN HC1 (100 mL). The resulting suspension was filtered, the filter-cake was dried to give the title compound as a white solid (3.3 g, 91 %). ?H NMR (400 MHz, DMSO-d6) oe 10.94 (s, 1H), 7.88 (s, 1H), 7.33 (s, 1H), 4.81 (s, 2H).
85%		Step 2. Iron powder (22.8 g, 408 mmol) was added to a solution of (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (2.28 g, 7.47 mmol) in acetic acid (230 mL), and the reaction mixture was heated at 60 C. over 150 min, cooled to room temperature, and filtered. The filtrate was evaporated, taken up in dichloromethane/methanol 1:1 and neutralized with 1 M aq. sodium carbonate solution. The organic layer was washed with water and the aqueous layer re-extracted with dichloromethane. The combined organic layers were washed again with 1 M aq. sodium carbonate solution, dried (Na2SO4), and evaporated to produce 7-bromo-1H-4-oxa-1,5-diaza-naphthalen-2-one (1.46 g, 85%). Off-white solid, MS (ISP)=226.9 (M-H)-.
	With acetic acid; zinc; In tetrahydrofuran; at 20 - 45℃; for 0.5h;	To a solution of ethyl [ (5-bromo-3-nitropyridin-2- yl) oxy] acetate (15.7 g) in THF (300 mL) was added acetic acid (150 mL) at room temperature, and then the mixture was <n="360"/>allowed to warm to 45C. Zinc (powder, 51 g) was added to the mixture at 450C, and the mixture was stirred at 45C for 0.5 hr. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, and ethyl acetate layer was washed with aqueous sodium bicarbonate solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was diluted with acetic acid (150 mL) , and the mixture was refluxed for 1 hr. The mixture was concentrated in vacuo, and the resulting crystals were suspended in ethyl acetate. The mixture was refluxed for 2 hr, and then cooled to room temperature. The resulting crystals were collected by filtration to give the title compound (9.8 g) .1H-NMR (300 MHz, DMSO-d6) delta: 4.81 (s, 2H), 7.33 (d, J = 2.3 Hz, IH), 7.88 (d, J = 2.3 Hz, IH), 10.94 (s, IH).

	With iron; acetic acid; at 80℃;	Compound 1b was synthesized from 9b using same procedure as mentioned for compound 1c. 1H NMR (300 MHz, DMSO-d6) = 4.82 (s, 2H)7.34 (s, 1 H) 7.86 ( s, 1 H) 11.0 ( s, 1 H); 13C NMR (300 MHz, DMSO-d6) delta ppm 66.83, 112.09 , 123.99 , 124.82 , 140.13 , 149.73 , 163.87; HRMS m/z (EI) calcd. for C7H5BrN2O2 227.9534, found 228.9675 [M+H]+
	With iron; acetic acid; at 25 - 60℃; for 3h;	Step 2: Preparation of 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one. [0603] To a mixture of ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate (17.5 g, 57.3 mmol) in anhydrous acetic acid (150 mL) was added Fe (48.9 g, 832 mmol) at 25 C. After stirring for 3 h at 60 C, the colour of the mixture was from yellow to black. TLC showed the reaction was almost completed. Acetic acid was removed under reduced pressure; the residue was diluted with DMF (500 mL), filtered and concentrated under reduced pressure. The residue was washed with EtOAc (20 mL) to give 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (26.7 g, crude) as a brick-red solid. NMR (400 MHz, DMSO-r e) d 4.82 (2H, s), 7.34 (1H, s), 7.89 (1H, s), 10.96 (1H, s).

Reference： [1]Patent: WO2018/237370,2018,A1 .Location in patent: Paragraph 0076; 00108; 00111; 001112
[2]Patent: US2007/191603,2007,A1 .Location in patent: Page/Page column 37
[3]Zeitschrift fur Chemie,1986,vol. 26,p. 99
[4]Patent: WO2007/77961,2007,A2 .Location in patent: Page/Page column 358
[5]Synthetic Communications,2013,vol. 43,p. 3315 - 3321
[6]Patent: WO2019/126731,2019,A1 .Location in patent: Paragraph 0603

4
[ 105544-30-7 ]
[ 107113-02-0 ]

Reference： [1]Zeitschrift fur Chemie,1986,vol. 26,p. 99

5
[ 67443-38-3 ]
[ 623-50-7 ]
[ 105544-30-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 1h;	Method I: 5-bromo-2-chloro-3-nitropyridine (100 mg, 0.42 mmol) and Ethyl glycolate (0.044 mL, 0.46 mmol) were dissolved in THF (5 mL) and cooled to 0C. Sodium hydride (0.015 mL, 0.46 mmol) was added and the mixture was stirred for 1hr at room temperature. Reaction mixture was poured in ice water and extracted with EtOAc (2 x 10ml). The organiclayer was washed with brine (10ml), dried over sodium sulphate and concentrated. The crude product was purified by flash column using 100-200 silica gel to ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (105 mg, 82 %) 9(b). 1H NMR (300 MHz, DMSO-d6) delta = 1.27 (s, 3H), 4.25 (q, 2 H), 5.12 (s, 2H) 8.40 (d, J = 2.07 Hz, 1 H), 8.47 (d, J = 2.07 Hz, 1 H); ESMS: m/z 306.8 [M+1]
71%	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 8h;	To a solution of 5-bromo-2-chloro-3-nitropyridine (6.0 g, 25.4 mmol) and <strong>[623-50-7]ethyl 2-hydroxyacetate</strong> (2.9 g, 28.0 mmol) in THF (150 mL) was added slowly 60 % NaH (1.3 g, 1.8 mmol) at 0 C. The mixture was stirred at room temperature for 8 h. After water (20 mL) was added to quench the reaction, the mixture was treated with brine (100 mL) and extracted with ethyl acetate (50 mL * 2). The combined organic layers were dried over Na2504, filtered and concentrated. Then the solid was filtered to give the title compound as a yellow solid (5.5 g 71 %). ?H NMR (400 MHz, CDC13) oe 8.46 (d, J = 2.0 Hz, 1H), 8.39 (d, J = 1.6 Hz, 1H), 5.05 (s, 2H), 4.26-4.17 (m, 2H), 1.28 (t, J= 7.2 Hz, 3H).
49%		Step 1. Sodium hydride (55% dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of <strong>[623-50-7]ethyl glycolate</strong> (1.43 g, 13.8 mmol) in 1,4-dioxane, and the reaction mixture was heated at 70 C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70 C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (Na2SO4), and evaporated. Chromatography (SiO2, hexane-ethyl acetate gradient) furnished (5-bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (1.03 g, 49%). Light yellow liquid, MS (ISP)=305.1 (M+H)+.

48%		Step 7: Preparation of ethyl 2-((5-bromo-3-nitropyri din-2 -yl)oxy)acetate. [0602] To a mixture of <strong>[623-50-7]ethyl 2-hydroxyacetate</strong> (14.0 g, 134 mmol) in anhydrous THF (150 mL) was added NaH (4.48 g, 112 mmol, 60% in mineral oil) at 0 C. After stirring for 30 min, 5-bromo-2-chloro-3-nitropyridine (26.6 g, 112 mmol) was added at 0 C, and the reaction mixture was stirred at 25 C for 15.5 h. TLC showed the reaction was almost completed. The colour of mixture was black. The residue was poured into water (150 mL) at 0 C and extracted with EtOAc (100 mL x3). The combined organic phase was dried over anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by Combi Flash (6% EtOAc in pentane) to give ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate (16.5 g, yield: 48%) as a yellow solid. NMR (400 MHz, CDCb) d 1.26 (3H, t, J= 12 Hz), 4.23 (2H, q, J= 12 Hz), 5.04 (2H, s), 8.39 (1H, d, J= 2.4 Hz), 8.46 (1H, d, J= 2.4 Hz).
44%		To a suspension of sodium hydride (5.31 g, 133 mmol) in 1 ,4-dioxane (250 ml), <strong>[623-50-7]ethyl glycolate</strong> (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1 ,4- dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and <strong>[623-50-7]ethyl glycolate</strong> was added drop wise over a period of 30 minutes at 0C. The resulting reaction mixture was heated to 80C overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by Biotage silica chromatography (gradient 0% to 10% ethyl acetate in n- hexanes) to give the title compound (1 .8g, 44%). N R (500 MHz, CDCI3): 8.48 (1 H, s), 8.42 (1 H, s), 5.07 (2H, s), 4.28-4.24 (2H, q), 1.31-1.28 (3H, t).
	With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h;	To a mixture of 5-bromo-2-chloro-3-nitropyridine (21.7 g) , <strong>[623-50-7]ethyl glycolate</strong> (11.4 g) , DMF (7.5 mL) and THF (90 mL) was added sodium hydride (60% in mineral oil, 6.6 g) under ice-cooling. The mixture was allowed to warm to room temperature, and stirred for 0.5 hr. The mixture was poured into ice-cooled water and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexane -» hexane:ethyl acetate = 4:1). Resulting crystals were collected by filtration, and washed with hexane. The title compound was obtained as crystals (15.8 g) .1H-NMR (300 MHz, DMSO-d6) delta: 1.18 (t, J = 7.0 Hz, 3H), 4.14 (q, J = 7.0 Hz, 2H), 5.11 (s, 2 H), 8.65 (d, J = 2.3 Hz, IH), 8.77 (d, J = 2.3 Hz, IH).

Reference： [1]Synthetic Communications,2013,vol. 43,p. 3315 - 3321
[2]Patent: WO2018/237370,2018,A1 .Location in patent: Paragraph 00108; 00109; 00110
[3]Patent: US2007/191603,2007,A1 .Location in patent: Page/Page column 37
[4]Patent: WO2019/126731,2019,A1 .Location in patent: Paragraph 0602
[5]Patent: WO2011/77098,2011,A1 .Location in patent: Page/Page column 157-158
[6]Patent: WO2007/77961,2007,A2 .Location in patent: Page/Page column 358

6
[ 105544-30-7 ]
[ 98-80-6 ]
[ 1313441-32-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With triphenylphosphine; cesium fluoride;palladium diacetate; In 1,2-dimethoxyethane; at 75℃;Inert atmosphere;	In a 11 round-bottomed flask was added <strong>[105544-30-7]ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate</strong> (18.33 g, 60.1 mmol), phenylboronic acid (10.99 g, 90 mmol), triphenylphosphine (4.73 g, 18.02 mmol) and cesium fluoride (45.6 g, 300 mmol) in 1 ,2-dimethoxyethane (300 ml) to give a yellow solution. The reaction mixture was degassed by bubbling nitrogen for 30 minutes. Palladium(ll) acetate (2.023 g, 9.01 mmol) was added and the mixture was heated to 75C under a nitrogen atmosphere overnight. The reaction mixture was allowed to cool to room temperature and concentrated to dryness under reduced pressure to give a brown solid. This was re-dissolved in dichloromethane, filtered and concentrated to dryness under reduced pressure to give a brown solid The crude residue was purified via Biotage chromatography (gradient 5% to 60% ethyl acetate in n- hexanes) to give the title compound (6.9g, 38%). H NMR (500 MHz, CDCI3) delta 8.58 (1 H, s), 8.56 (1 H, s), 7.59-7.52 (2H, m), 7.48-7.46 (2H, m), 7.45-7.43 (1 H, m), 5.13 (2H, s), 4.30-4.26 (2H, q), 1.33-1.30 (3H, t).

Reference： [1]Patent: WO2011/77098,2011,A1 .Location in patent: Page/Page column 158

7
[ 105544-30-7 ]
[ 1198154-03-8 ]

Reference： [1]Patent: WO2011/77098,2011,A1

8
[ 105544-30-7 ]
[ 1313441-33-6 ]

Reference： [1]Patent: WO2011/77098,2011,A1

9
[ 105544-30-7 ]
2-((1r,3r)-3-hydroxy-3-methyl-1-(4-(1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

10
[ 105544-30-7 ]
6-(4-((1r,3r)-1-amino-3-hydroxy-3-methylcyclobutyl)phenyl)-1-methyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

11
[ 105544-30-7 ]
[ 1313441-54-1 ]

Reference： [1]Patent: WO2011/77098,2011,A1

12
[ 105544-30-7 ]
[ 1313441-55-2 ]

Reference： [1]Patent: WO2011/77098,2011,A1

13
[ 105544-30-7 ]
2-((1r,3r)-1-(4-(1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)-3-hydroxy-3-methylcyclobutyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

14
[ 105544-30-7 ]
(1r,3r)-3-amino-3-(4-(1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)-1-methylcyclobutanol [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

15
[ 105544-30-7 ]
[ 1313441-64-3 ]

Reference： [1]Patent: WO2011/77098,2011,A1

16
[ 105544-30-7 ]
[ 1313441-65-4 ]

Reference： [1]Patent: WO2011/77098,2011,A1

17
[ 105544-30-7 ]
2-(6-(4-(aminomethyl)phenyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)acetonitrile trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

18
[ 105544-30-7 ]
[ 1313485-80-1 ]

Reference： [1]Patent: WO2011/77098,2011,A1

19
[ 105544-30-7 ]
[ 1313441-66-5 ]

Reference： [1]Patent: WO2011/77098,2011,A1

20
[ 105544-30-7 ]
tert-butyl ((1s,3s)-1-(4-(1-ethyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)-3-hydroxycyclobutyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

21
[ 105544-30-7 ]
(1s,3s)-3-amino-3-(4-(1-ethyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanol [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

22
[ 105544-30-7 ]
2-((1r,3r)-1-(4-(1-ethyl-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)-3-hydroxy-3-methylcyclobutyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2011/77098,2011,A1

23
[ 105544-30-7 ]
tetrahydro-2H-pyran-4-yl-7-(2-((tert-butoxycarbonyl)amino)benzo[d]thiazol-6-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/237370,2018,A1

24
[ 105544-30-7 ]
[ 946121-78-4 ]

Reference： [1]Patent: WO2018/237370,2018,A1
[2]Patent: WO2019/126731,2019,A1

25
[ 105544-30-7 ]
cyclohexyl-7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/237370,2018,A1

26
[ 105544-30-7 ]
cyclohexyl-7-(2-acetamidobenzo[d]thiazol-6-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/237370,2018,A1

27
[ 105544-30-7 ]
tetrahydro-2H-pyran-4-yl-7-bromo-2,3-dihydro-1H-pyrido[2,3-h][1,4]oxazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/237370,2018,A1

28
[ 105544-30-7 ]
tetrahydro-2H-pyran-4-yl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/237370,2018,A1

29
[ 105544-30-7 ]
1-(4-(6-((1-acetyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)amino)pyridin-3-yl)phenyl)pyrrolidin-2-one [ No CAS ]