[ CAS No. 20348-23-6 ]

Name: 20348-23-6|3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine|97%
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Quality Control of [ 20348-23-6 ]

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SDS Specification

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Product Details of [ 20348-23-6 ]

CAS No. :	20348-23-6	MDL No. :	MFCD09025907
Formula :	C₇H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QQVXDMFULJVZLA-UHFFFAOYSA-N
M.W :	136.15 g/mol	Pubchem ID :	13196538
Synonyms :

Calculated chemistry of [ 20348-23-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.86
TPSA :	34.15 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	0.31
Log Po/w (MLOGP) :	0.28
Log Po/w (SILICOS-IT) :	1.43
Consensus Log Po/w :	0.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.7
Solubility :	2.71 mg/ml ; 0.0199 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	8.34 mg/ml ; 0.0613 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.34
Solubility :	0.627 mg/ml ; 0.0046 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 20348-23-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20348-23-6 ]

* 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 [ 20348-23-6 ]
Downstream synthetic route of [ 20348-23-6 ]

[ 20348-23-6 ] Synthesis Path-Upstream 1~7

1
[ 20348-23-6 ]
[ 34950-82-8 ]

Yield	Reaction Conditions	Operation in experiment
69.5%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 2 h;	To a solution of 3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazine (500 mg, 3.67 mmol) in DMF (10 mL) was added NBS (719 mg, 4.04 mmol) at 0°C. The mixture was stirred at 0°C for 2 h. The mixture was quenched with sat. NaHCO₃ aq. ' and water at 0°C and stirred at 0°C for 20 min. The precipitate was collected by filtration. The solid was washed with water and dried in vacuo to give the title compound (549 mg, 2.55 mmol, 69.5percent) as brown solids. ^{. .} (3284) MS (ESI+), found 215.2 (M+H) (3285) ¹H NMR (300 MHz, CDC1₃) 5:3.50-3.58 (2H, m) , 4.18-4.26 (2H, m) , 4.82 (1H, brs), 7.10 (1H, d, J = 1.9 Hz), 7.72 (1H, d, J = 2.3 Hz)
28%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1 h;	(Example 5 Synthesis of Compounds I-114, I-110, and I-111) [Show Image][Show Image]Step 1 To a solution of Compound (14) (4.00 g, 29.4 mmol) in dimethylformamide (40 mL), N-bromosuccinimide (6.27 g, 35.3 mmol) was added. The solution was then stirred at room temperature for 1 hour. Aqueous saturated sodium bicarbonate (100 mL) and water (100 mL) were then thereto. The precipitated powder was filtered, and then washed with water. The filtrate was then extracted with diisopropyl ether. The organic layer was washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield subject compound (15) (1.79 g, 28percent) as a pale yellow powder.¹H-NMR (DMSO-d₆) δ7.62 (1H, d, J= 2.1Hz), 7.14 (1H, d, J =2.1Hz), 6.98 (1H, br s), 4.11 (2H, t, J=4.5Hz), 3.36-3.40 (2H, m) LC/MS (Method A): 0.98 min, [M+H]⁺= 217.0.

Reference： [1] Patent: WO2018/30550, 2018, A1, . Location in patent: Paragraph 0596
[2] Patent: EP2341052, 2011, A1, . Location in patent: Page/Page column 40
[3] Acta Chemica Scandinavica (1947-1973), 1971, vol. 25, p. 3135 - 3143
[4] Patent: KR101576386, 2015, B1, . Location in patent: Paragraph 0158-0160

2
[ 20348-09-8 ]
[ 20348-23-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 18 h; Heating / reflux Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃;	a) 3,4-Dihydro-2H-pyrido[3,2-_{][l,4]oxazine; To an ice-cold solution of 4H-ρyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TηF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TηF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 0}0_{C and quenched the reaction with H&2}O (4 mL) followed by NaOH (4 mL, 15percent) and H₂O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85percent) as a blue-gray powder: ¹H NMR (500 MHz, OMSO-d₆) δ 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e \\31 (M + η)\\
79%	With sodium hydroxide; LiAlH₄ In tetrahydrofuran	a) 3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine To a suspension of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g, 13.3 mmole) in dry THF (40 mL) was added a solution of LiAlH₄ in THF (1.0 M, 26.6 mL, 26.6 mmole) slowly at 0°C. After 1 hr the mixture was quenched with 2.0 M NaOH until a solid formed. The mixture was dried (MgSO₄), filtered, and concentrated under reduced pressure to give the title compound (1.44 g, 79percent) as a white solid which was sufficiently pure for use in the next step: MS (ES) m/e 137 (M + H)⁺.

Reference： [1] Patent: WO2007/53131, 2007, A2, . Location in patent: Page/Page column 133
[2] Patent: EP1226138, 2004, B1,
[3] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324
[4] Patent: US2008/305169, 2008, A1,
[5] Patent: US2007/10670, 2007, A1, . Location in patent: Page/Page column 92
[6] Patent: US2008/64871, 2008, A1, . Location in patent: Page/Page column 56

3
[ 34950-82-8 ]
[ 20348-23-6 ]

Yield	Reaction Conditions	Operation in experiment
17%	With potassium carbonate; tricyclohexylphosphine In water; toluene at 115℃; for 96 h; Inert atmosphere; Sealed tube	In an open sealed tube, a stirred mixture of 7-bromo-3,4-dihydro-2-pyrido[3,2- b][l,4]oxazoline (Maybridge, United Kingdom) (108 mg, 0.5 mmol), palladium(II) acetate (11 mg, 0.05 mmol), tricyclohexylphosphine (28 mg, 0.1 mmol), K₂C0₃ (276 mg, 2.0 mmol) and ira/i5^,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (159 mg, 0.6 mmol) in toluene (3 mL) and H₂0 (1 mL) was de-gassed with N₂ for 15 minutes, then the reaction mixture placed under nitrogen, heated to 115 °C and stirred for 4 days. After allowing to cool, the reaction mixture was filtered through Celite and the filter cake washed with EtOAc (3 x 20 mL), H₂0 (10 mL) and EtOAc (20 mL). The aqueous and organic layers of the filtrate were partitioned and the aqueous layer extracted with EtOAc (1 x 20 mL). The combined organic extracts were dried (Na₂S0₄), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (4 prep TLC plates used) using EtOAc as eluent to give the product (21 mg, 17percent) as a solid.[00232] 1H NMR (CDC1₃, 300MHz): δ 7.54 (s, 1H), 6.70 (d, / = 1.6 Hz, 1H), 4.99 (br. s, 1H), 4.21 (dt, / = 4.4, 0.7 Hz, 2H), 3.53 (t, / = 4.4 Hz, 2H), 2.26-2.19 (m, 1H), 1.74-1.61 (m, 1H), 1.33-1.26 (m, 1H), 1.10-1.03 (m, 1H). ¹³C NMR (CDC1₃, 75MHz): δ 146.6, 139.8, 138.8, 128.0 (q, / = 269 Hz), 125.4, 120.7, 65.0, 40.8, 22.7 (q, / = 36.7 Hz), 17.0 (q, / = 2.8 Hz), 10.2 (q, J = 2.2 Hz). ¹⁹F NMR (CDC1₃, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = 245.09 (M+H)⁺ HRMS (EI): [M+H]⁺ calc'd for C11H11F3N2O m/z 245.0902, found 245.0909.[00233] Also obtained from the preparative thin-layer chromatography plates was recovered 7-bromo-3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (18 mg, 17percent) and reduced starting material, 3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (9.4 mg, 14percent). Note: the above reaction also was successfully undertaken using the alternative ligands 2- dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, or 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl.

Reference： [1] Patent: WO2012/75316, 2012, A2, . Location in patent: Page/Page column 55

4
[ 149-73-5 ]
[ 20348-23-6 ]

Reference： [1] Patent: US2015/119385, 2015, A1, . Location in patent: Paragraph 0692; 0693
[2] Patent: WO2015/59668, 2015, A1, . Location in patent: Page/Page column 106

5
[ 16867-03-1 ]
[ 20348-23-6 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324

6
[ 959992-62-2 ]
[ 20348-23-6 ]

Reference： [1] Patent: US2015/119385, 2015, A1,

7
[ 959992-62-2 ]
[ 20348-23-6 ]

Reference： [1] Patent: WO2015/59668, 2015, A1,

[ 20348-23-6 ] Synthesis Path-Downstream 1~59

1
[ 20348-23-6 ]
[ 34950-82-8 ]

Yield	Reaction Conditions	Operation in experiment
69.5%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 2h;	To a solution of 3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazine (500 mg, 3.67 mmol) in DMF (10 mL) was added NBS (719 mg, 4.04 mmol) at 0C. The mixture was stirred at 0C for 2 h. The mixture was quenched with sat. NaHCO3 aq. ' and water at 0C and stirred at 0C for 20 min. The precipitate was collected by filtration. The solid was washed with water and dried in vacuo to give the title compound (549 mg, 2.55 mmol, 69.5%) as brown solids. . . (3284) MS (ESI+), found 215.2 (M+H) (3285) 1H NMR (300 MHz, CDC13) 5:3.50-3.58 (2H, m) , 4.18-4.26 (2H, m) , 4.82 (1H, brs), 7.10 (1H, d, J = 1.9 Hz), 7.72 (1H, d, J = 2.3 Hz)
28%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 1h;	(Example 5 Synthesis of Compounds I-114, I-110, and I-111) [Show Image][Show Image]Step 1 To a solution of Compound (14) (4.00 g, 29.4 mmol) in dimethylformamide (40 mL), N-bromosuccinimide (6.27 g, 35.3 mmol) was added. The solution was then stirred at room temperature for 1 hour. Aqueous saturated sodium bicarbonate (100 mL) and water (100 mL) were then thereto. The precipitated powder was filtered, and then washed with water. The filtrate was then extracted with diisopropyl ether. The organic layer was washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield subject compound (15) (1.79 g, 28%) as a pale yellow powder.1H-NMR (DMSO-d6) delta7.62 (1H, d, J= 2.1Hz), 7.14 (1H, d, J =2.1Hz), 6.98 (1H, br s), 4.11 (2H, t, J=4.5Hz), 3.36-3.40 (2H, m) LC/MS (Method A): 0.98 min, [M+H]+= 217.0.
	With bromine; acetic acid; at 0℃; for 3h;	AcOH (18 mL) in Fig. 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (1.00 g, 7.35 mmol) to a stirring solution of Br2 (0.472 mL, 9.19 mmol) was added dropwise at 0 C. After stirring the mixture resulting as a result from 0 C for 3 hours, it was warmed to ambient temperature such that the mixture. After the precipitate was filtered, diluted with EtOAc (200 mL) and dried in a high vacuum state was produced F1.

Reference： [1]Patent: WO2018/30550,2018,A1 .Location in patent: Paragraph 0596
[2]Patent: EP2341052,2011,A1 .Location in patent: Page/Page column 40
[3]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143
[4]Patent: KR101576386,2015,B1 .Location in patent: Paragraph 0158-0160

2
[ 20348-09-8 ]
[ 20348-23-6 ]

Yield	Reaction Conditions	Operation in experiment
85%		a) 3,4-Dihydro-2H-pyrido[3,2-&][l,4]oxazine; To an ice-cold solution of 4H-rhoyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TetaF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TetaF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H2O (4 mL) followed by NaOH (4 mL, 15%) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85%) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) delta 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e 31 (M + eta)
79%	With sodium hydroxide; LiAlH4; In tetrahydrofuran;	a) 3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine To a suspension of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g, 13.3 mmole) in dry THF (40 mL) was added a solution of LiAlH4 in THF (1.0 M, 26.6 mL, 26.6 mmole) slowly at 0C. After 1 hr the mixture was quenched with 2.0 M NaOH until a solid formed. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.44 g, 79%) as a white solid which was sufficiently pure for use in the next step: MS (ES) m/e 137 (M + H)+.
	With sodium hydroxide; In tetrahydrofuran; water;	Step 1 Production of 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine Lithium aluminum hydride (2 g) was suspended in tetrahydrofuran (80 mL), and <strong>[20348-09-8]4H-pyrido[3,2-b][1,4]oxazin-3-one</strong> (3.956 g) was added under ice-cooling by small portions. After heating under reflux for 2 hrs, water (2 mL), 15% aqueous sodium hydroxide (2 mL) and water (6 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate=1:9) to give the title compound (3.407 g) as a white solid.

		Step 1 Production of 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine Lithium aluminum hydride (2 g) was suspended in tetrahydrofuran (80 mL), and <strong>[20348-09-8]4H-pyrido[3,2-b][1,4]oxazin-3-one</strong> (3.956 g) was added under ice-cooling by small portions. After heating under reflux for 2 hrs, water (2 mL), 15% aqueous sodium hydroxide (2 mL) and water (6 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate=1:9) to give the title compound (3.407 g) as a white solid.
		Step 1 Production of 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine Lithium aluminum hydride (2 g) was suspended in tetrahydrofuran (80 mL), and <strong>[20348-09-8]4H-pyrido[3,2-b][1,4]oxazin-3-one</strong> (3.956 g) was added under ice-cooling by small portions. After heating under reflux for 2 hrs, water (2 mL), 15% aqueous sodium hydroxide (2 mL) and water (6 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate=1:9) to give the title compound (3.407 g) as a white solid.

Reference： [1]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 133
[2]Patent: EP1226138,2004,B1
[3]Acta Chemica Scandinavica (1947),1969,vol. 23,p. 2322 - 2324
[4]Patent: US2008/305169,2008,A1
[5]Patent: US2007/10670,2007,A1 .Location in patent: Page/Page column 92
[6]Patent: US2008/64871,2008,A1 .Location in patent: Page/Page column 56

3
[ 20348-23-6 ]
[ 100-39-0 ]
[ 19612-61-4 ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

4
[ 20348-23-6 ]
[ 109-54-6 ]
[ 19612-60-3 ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

5
[ 20348-23-6 ]
[ 106-95-6 ]
4-allyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

6
[ 20348-23-6 ]
[ 107-13-1 ]
[ 34950-71-5 ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

7
[ 20348-23-6 ]
C-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-methylamine [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

8
[ 20348-23-6 ]
[ 34945-66-9 ]

Reference： [1]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 3135 - 3143

9
[ 16867-03-1 ]
[ 20348-23-6 ]

Reference： [1]Acta Chemica Scandinavica (1947),1969,vol. 23,p. 2322 - 2324

10
[ 20348-23-6 ]
[ 354575-15-8 ]
(4-benzyloxy-3,5-dichlorophenyl)-(2,3-dihydropyrido[3,2-b][1,4]oxazin-4-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; at 20℃; for 12h;	Step 2 Production of (4-benzyloxy-3,5-dichlorophenyl)-(2,3-dihydropyrido[3,2-b][1,4]oxazin-4-yl)-methanone 3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazine (272 mg) was dissolved in chloroform (15 mL), and triethylamine (0.335 mL) and 4-benzyloxy-3,5-dichlorobenzoyl chloride (662 mg) obtained in Step 3 of Example 8 were added under ice-cooling. The mixture was stirred at room temperature for 12 hrs, and the reaction mixture was purified by silica gel chromatography (n-hexane-ethyl acetate=4:1) to give the title compound (646 mg) as a white solid.
	With triethylamine; In chloroform; at 0 - 40℃; for 12h;	Step 2 Production of (4-benzyloxy-3,5-dichlorophenyl)-(2,3-dihydropyrido[3,2-b][1,4]oxazin-4-yl)-methanone 3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazine (272 mg) was dissolved in chloroform (15 mL), and triethylamine (0.335 mL) and 4-benzyloxy-3,5-dichlorobenzoyl chloride (662 mg) obtained in Step 3 of Example 8 were added under ice-cooling. The mixture was stirred at room temperature for 12 hrs, and the reaction mixture was purified by silica gel chromatography (n-hexane-ethyl acetate=4:1) to give the title compound (646 mg) as a white solid.

Reference： [1]Patent: US2007/10670,2007,A1 .Location in patent: Page/Page column 92
[2]Patent: US2008/64871,2008,A1 .Location in patent: Page/Page column 56

11
[ 20348-23-6 ]
7-bromo-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With bromine; acetic acid; at 0 - 20℃; for 5h;	b) 7-Bromo-2,2-dimethyl-3,4-dihydro-2H-rhoyrido[3,2-6][l,4]oxazine hydrogen bromide; To an ice-cold solution of 3,4-dihydro-2H-pyrido[3,2-&][l,4]oxazine (3.86 g, 28.3 mmol) in acetic acid (71.7 mL) was added Br2 (1.83 mL, 35.6 mmol). The mixture was stirred for 3 h at 00C then warmed to ambient temperature. After 2 h, the resulting solids were collected by filtration and washed with EtOAc (400 mL). The solids were dried to give the title compound (6.31 g, 60%) as a dark orange powder: 1H NMR (300 MHz, DMSO-4) delta 12.25 (br s, IH), 7.77 (t; J= 1.8 Hz, IH), 7.45 (t, J= 2.1 Hz, IH), 4.20 (t, J= 4.6 Hz, 2H), 3.48 (t, J= 4.6 Hz, 2H); MS (ESl) m/e 215 (M + H)+.

Reference： [1]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 133

12
[ 20348-23-6 ]
[ 24424-99-5 ]
[ 335030-28-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ammonium chloride; In tetrahydrofuran;	b) 4-(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazine To a solution of 3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazine (1.44 g, 10.6 mmole) and di-tert-butyl dicarbonate (2.78 g, 12.7 mmole) in dry THF (50 mL) was added a solution of LiHMDS in THF (1.0 M, 12.7 mL, 12.7 mmole) dropwise at 0C. After 30 min the mixture was quenched with saturated NH4Cl and extracted with EtOAc (3x). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash chromatography on silica gel (40% EtOAc/hexanes) gave the title compound (2.0 g, 80%) as a clear oil: MS (ES) m/e 237 (M + H)+.

Reference： [1]Patent: EP1226138,2004,B1

13
[ 20348-23-6 ]
[ 888730-53-8 ]
[ 354575-15-8 ]
(4-benzyloxy-3,5-dichlorophenyl)-(2,3-dihydropyrido[3,2-b][1,4]oxazin-4-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 2-nitro-4-(pyrrolidine-1-sulfonyl)phenol; chloroform;	Step 2 Production of (4-benzyloxy-3,5-dichlorophenyl)-(2,3-dihydropyrido[3,2-b][1,4]oxazin-4-yl)-methanone 3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazine (272 mg) was dissolved in chloroform (15 mL), and triethylamine (0.335 mL) and 4-benzyloxy-3,5-dichlorobenzoyl chloride (662 mg) obtained in Step 3 of Reference Example 8 were added under ice-cooling. The mixture was stirred at room temperature for 12 hrs, and the reaction mixture was purified by silica gel chromatography (n-hexane-ethyl acetate=4:1) to give the title compound (646 mg) as a white solid.

Reference： [1]Patent: US2008/305169,2008,A1

14
[ 20348-23-6 ]
[ 252742-72-6 ]
C₁₀H₁₁N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		A solution of 33A (0.105 g 0.77 mmol) in DMF (5 mL) was treated with KN(SiMe3)2 (0.5 M/toluene, 1.8 mL, 0.93 mmol), stirred at 0° C. for 20 min, and then treated with 33B (0.155 g 1.16 mmol, Tetrahedron Letters 2000, 41, 8661). The reaction was warmed to 20° C., stirred 2 h, and concentrated. The residue was then treated with 0.5 N NaOH (10 mL) and washed with CH2Cl2 (3.x.). The aqueous layer was concentrated and subjected to chromatography (20-80percent EtOAc/hexanes) to provide 33 as a white solid (0.065 g, 36percent). LMCS m/z 234 (MH+).

Reference： [1]Patent: US2007/93477,2007,A1 .Location in patent: Page/Page column 41

15
[ 20348-23-6 ]
[ 1214927-92-0 ]

Reference： [1]Patent: EP2341052,2011,A1

16
[ 20348-23-6 ]
[ 1214927-84-0 ]

Reference： [1]Patent: EP2341052,2011,A1

17
[ 20348-23-6 ]
[ 1214927-86-2 ]

Reference： [1]Patent: EP2341052,2011,A1

18
[ 20348-23-6 ]
[ 1214928-28-5 ]

Reference： [1]Patent: EP2341052,2011,A1

19
[ 20348-23-6 ]
C₂₇H₂₂N₄O₂ [ No CAS ]

Reference： [1]Patent: EP2341052,2011,A1

20
[ 20348-23-6 ]
[ 1214928-60-5 ]

Reference： [1]Patent: EP2341052,2011,A1

21
[ 20348-23-6 ]
[ 1214928-81-0 ]

Reference： [1]Patent: EP2341052,2011,A1

22
[ 20348-23-6 ]
[ 1214928-83-2 ]

Reference： [1]Patent: EP2341052,2011,A1

23
trans-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester [ No CAS ]
[ 34950-82-8 ]
[ 20348-23-6 ]
trans-7-(2-(trifluoromethyl)cyclopropyl)-3,4-dihydro-2-pyrido[3,2-b][1,4]oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%; 17%	With potassium carbonate; tricyclohexylphosphine;palladium diacetate; In water; toluene; at 115℃; for 96h;Inert atmosphere; Sealed tube;	In an open sealed tube, a stirred mixture of 7-bromo-3,4-dihydro-2-pyrido[3,2- b][l,4]oxazoline (Maybridge, United Kingdom) (108 mg, 0.5 mmol), palladium(II) acetate (11 mg, 0.05 mmol), tricyclohexylphosphine (28 mg, 0.1 mmol), K2C03 (276 mg, 2.0 mmol) and ira/i5,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (159 mg, 0.6 mmol) in toluene (3 mL) and H20 (1 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, heated to 115 C and stirred for 4 days. After allowing to cool, the reaction mixture was filtered through Celite and the filter cake washed with EtOAc (3 x 20 mL), H20 (10 mL) and EtOAc (20 mL). The aqueous and organic layers of the filtrate were partitioned and the aqueous layer extracted with EtOAc (1 x 20 mL). The combined organic extracts were dried (Na2S04), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (4 prep TLC plates used) using EtOAc as eluent to give the product (21 mg, 17%) as a solid.[00232] 1H NMR (CDC13, 300MHz): delta 7.54 (s, 1H), 6.70 (d, / = 1.6 Hz, 1H), 4.99 (br. s, 1H), 4.21 (dt, / = 4.4, 0.7 Hz, 2H), 3.53 (t, / = 4.4 Hz, 2H), 2.26-2.19 (m, 1H), 1.74-1.61 (m, 1H), 1.33-1.26 (m, 1H), 1.10-1.03 (m, 1H). 13C NMR (CDC13, 75MHz): delta 146.6, 139.8, 138.8, 128.0 (q, / = 269 Hz), 125.4, 120.7, 65.0, 40.8, 22.7 (q, / = 36.7 Hz), 17.0 (q, / = 2.8 Hz), 10.2 (q, J = 2.2 Hz). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = 245.09 (M+H)+ HRMS (EI): [M+H]+ calc'd for C11H11F3N2O m/z 245.0902, found 245.0909.[00233] Also obtained from the preparative thin-layer chromatography plates was recovered 7-bromo-3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (18 mg, 17%) and reduced starting material, 3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (9.4 mg, 14%). Note: the above reaction also was successfully undertaken using the alternative ligands 2- dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, or 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl.

Reference： [1]Patent: WO2012/75316,2012,A2 .Location in patent: Page/Page column 55

24
[ 20348-23-6 ]
[ 380893-61-8 ]
4-[(5-bromo-2-pyridyl)methyl]-2,3-dihydropyrido[3,2-b][1,4]oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;Reflux;	To a solution of (5-bromo-2-pyridyl)methyl methanesulfonate (514.2 mg, 1 .93 mmol) in THF (6 ml_) and DIPEA (0.69 ml_, 3.86 mmol) was added to the corresponding amine (1 .2 eq). The reaction mixture was heated under reflux overnight, cooled and concentrated under reduced pressure. Further purification by flash column chromatography (DCM/MeOH containing 3% 7N NH3 in MeOH 100:0 to 90:10) afforded 4-[(5-bromo-2-pyridyl)methyl]-2,3-dihydropyrido[3,2-Jb][1 ,4]oxazine (520.6 mg, 1 .70 mmol, 88% yield) as a brown oil. UPLC-MS (ES+, Short acidic): 1 .04 min, m/z 308.1 [M+H]+

Reference： [1]Patent: WO2014/188173,2014,A1 .Location in patent: Paragraph 00423

25
3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-¹³C-carbaldehyde [ No CAS ]
[ 149-73-5 ]
[ 20348-23-6 ]
6-(dimethoxymeth-¹³C-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In methanol; at 50℃; for 5h;	[0692] A solution of 6-bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (193 mg, 0.897 mmol) in THF (4ml) at -78C. was treated with methyllithium (1.6 M in Et20, 0.56 ml,0.90 mmol) and stirred for 10 min. Then, n-BuLi (1.6 Minhexane, 0.67 ml, 1.1 mmol) was added drop wise and thereaction mixture was stirred for 1 h. The reaction mixture waswarmed to -50 C. and allowed to warm to -20 C. over 30min. The reaction mixture was cooled to -78 C. and thenmore n-BuLi (1.6 M in hexane, 0.28 ml, 0.45 mmol) wasadded. The reaction mixture was warmed to -50 C. andallowed to warm to -20 C. over 30 min. The reaction mixturewas cooled to -78 C. and treated with N,N-dimethylform-13C-amide (399 mg, 5.38 mmol), stirred at -78 C. for 45min. The reaction mixture was quenched by addition of sat.aq. NH4 Cl, warmed to room temperature, extracted withDCM (3x). The combined organic layers were dried overNa2S04 , filtered and concentrated under reduced pressure.The crude material was purified by normal phase chromatography(12 g silica gel cartridge, heptanes/EtOAc 100:0 to0:100) to give 87 mg of3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-13C-carbaldehyde as a yellow resin.[0693] A solution of this material in MeOH (2 ml) wastreated with p-toluenesulfonic acid monohydrate (10 mg,0.053 mmol) and trimethyl orthoformate (1.0 ml, 9.05 mmol),heated to 50 C. and stirred for 5 h. The heating was turned offand the reaction was stirred 16 h at room temperature. Thereaction mixture was treated with sat. aq. NaHC03 and concentrated.The residue was treated with water and extractedwith DCM (3x ). The combined organic layers were dried overNa2S04 , filtered and concentrated. The crude material waspurified by normal phase chromatography ( 4 g silica gelcartridge, heptanes/EtOAc 100:0 to 0:100) to give the titlecompound in a -2:1 mixture with 3,4-dihydro-2H-pyrido[3,2-b ][1,4]oxazine as a light yellow oil. (UPLC-MS 3) tR 0.50min; ESI-MS 212.1 [M+Ht.
	With toluene-4-sulfonic acid; In methanol; water; at 20 - 50℃; for 21h;	A solution of this material in MeOH (2 ml) was treated with p-toluenesulfonic acid monohydrate (10 mg, 0.053 mmol) and trimethyl orthoformate (1 .0 ml, 9.05 mmol), heated to 50 C and stirred for 5h. The heating was turned off and the reaction was stirred 16 h at room temperature. The reaction mixture was treated with sat. aq. NaHCO3 and concentrated. The residue was treated with water and extracted with DCM (3x).The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound in a -2:1 mixture with 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as a light yellow oil. (UPLC-MS 3) tR 0.50 mm; ESI-MS 212.1 [M+H].

Reference： [1]Patent: US2015/119385,2015,A1 .Location in patent: Paragraph 0692; 0693
[2]Patent: WO2015/59668,2015,A1 .Location in patent: Page/Page column 106

26
[ 959992-62-2 ]
[ 20348-23-6 ]

Reference： [1]Patent: US2015/119385,2015,A1

27
[ 959992-62-2 ]
[ 20348-23-6 ]
6-(dimethoxymeth-¹³C-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine [ No CAS ]

Reference： [1]Patent: WO2015/59668,2015,A1

28
[ 20348-23-6 ]
C₁₅H₁₄BrFN₂O₂ [ No CAS ]

Reference： [1]Patent: KR101576386,2015,B1

29
[ 20348-23-6 ]
C₂₈H₂₆FN₃O₂ [ No CAS ]

Reference： [1]Patent: KR101576386,2015,B1

30
[ 20348-23-6 ]
C₁₅H₁₆FN₃O₂ [ No CAS ]

Reference： [1]Patent: KR101576386,2015,B1

31
[ 20348-23-6 ]
[ 1189-71-5 ]
C₁₇H₁₅F₂N₃OS*ClH [ No CAS ]
C₂₅H₂₂F₂N₆O₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22 mg		To a solution of 0.1 M sulfurisocyanatidic chloride in DCM (2.88 mL, 0.288 mmol) was added a solution of Intermediate ZY-5 (100 mg, 0.288 mmol) in DCM (2 mL) at -15 C dropwise. The reaction mixture was then stirred at -15 C for 30 min. Then 3,4-dihydro- 2H-pyrido[3,2-b][l,4]oxazine (39.2 mg, 0.288 mmol) and TEA (0.160 mL, 1.15 mmol) were added and the reaction solution was stirred at rt for 30 min. The solvent was removed in vacuo and the residue was taken up into DMF (1 mL), filtered, and purified by preparative HPLC to afford the title compound (22 mg) as a white solid. LC-MS retention time = 1.07 min; m/z = 589.15 [M+H]+. (Start % B = 0, Final % B = 100, Gradient Time = 2 min, Flow Rate = 1.0 mL/min, Wavelength = 220, Solvent Pair = Water/Acetonitrile/TFA, Solvent A = 10%acetonitrile/90% Water/ 0.1 % TFA, Solvent B = 90% Acetonitrile/10%water/0.1% TFA, Column = Phenomenex Luna 30 x 2.0 MM 3muiotaeta Oven Temp. = 40 C).

Reference： [1]Patent: WO2016/172424,2016,A1 .Location in patent: Page/Page column 245

32
[ 20348-23-6 ]
N-(3-fluoro-4-sulfamoylbenzyl)-4-(2-(methoxymethyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

33
[ 20348-23-6 ]
N-(3-fluoro-4-(methylsulfamoyl)benzyl)-4-(2-(methoxymethyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

34
[ 20348-23-6 ]
[ 335030-30-3 ]

Reference： [1]Patent: WO2018/30550,2018,A1

35
[ 20348-23-6 ]
methyl 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylate [ No CAS ]
4-tert-butyl 7-methyl 2H-pyrido [3,2-b][1,4]oxazine-4,7(3H)-dicarboxylate [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

36
[ 20348-23-6 ]
4-(5-fluoro-2-(methoxymethyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

37
[ 20348-23-6 ]
4-(5-fluoro-2-(methoxymethyl)benzyl)-N-(4-sulfamoylbenzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

38
[ 20348-23-6 ]
methyl 4-((5-fluoro-3-(methoxymethyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

39
[ 20348-23-6 ]
4-((5-fluoro-3-(methoxymethyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

40
[ 20348-23-6 ]
4-((5-fluoro-3-(methoxymethyl)pyridin-2-yl)methyl)-N-(4-sulfamoylbenzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

41
[ 20348-23-6 ]
4-(2,3-difluoro-6-(methoxymethyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

42
[ 20348-23-6 ]
4-(2,3-difluoro-6-(methoxymethyl)benzyl)-N-(4-sulfamoylbenzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

43
[ 20348-23-6 ]
4-(2-(methoxymethyl)benzyl)-N-((1-(methylsulfonyl)piperidin-4-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

44
[ 20348-23-6 ]
4-(2-(methoxymethyl)benzyl)-N-((5-(methylsulfonyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

45
[ 20348-23-6 ]
N-(1-(4-bromophenyl)cyclopropyl)-4-(2-(methoxymethyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

46
[ 20348-23-6 ]
4-(2-(methoxymethyl)benzyl)-N-(1-(4-(methylsulfonyl)phenyl)cyclopropyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1
[2]Patent: WO2018/30550,2018,A1

47
[ 20348-23-6 ]
3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

48
[ 20348-23-6 ]
N-(4-(methylsulfonyl)benzyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

49
[ 20348-23-6 ]
4-(3,5-dicyclopropylphenyl)-N-(4-(methylsulfonyl)benzyl)-3.4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

50
[ 20348-23-6 ]
methyl 4-(3,5-dicyclopropylphenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

51
[ 20348-23-6 ]
4-(3,5-dicyclopropylphenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

52
[ 20348-23-6 ]
4-(3,5-dicyclopropylphenyl)-N-((5-(ethylsulfonyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

53
[ 20348-23-6 ]
4-(3,5-dicyclopropylphenyl)-N-((1-(methylsulfonyl)piperidin-4-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

54
[ 20348-23-6 ]
4-(3,5-dicyclopropylphenyl)-N-((5-(methylsulfonyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

55
[ 20348-23-6 ]
methyl 4-(2,6-dicyclopropylpyridin-4-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

56
[ 20348-23-6 ]
4-(2,6-dicyclopropylpyridin-4-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

57
[ 20348-23-6 ]
4-(2,6-dicyclopropylpyridin-4-yl)-N-((5-(methylsulfonyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

58
[ 20348-23-6 ]
4-(2,6-dicyclopropylpyridin-4-yl)-N-((5-(ethylsulfonyl)pyridin-2-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

59
[ 20348-23-6 ]
4-(2,6-dicyclopropylpyridin-4-yl)-N-((1-(methylsulfonyl)piperidin-4-yl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/30550,2018,A1

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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
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
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
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
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
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. 20348-23-6 ]

Quality Control of [ 20348-23-6 ]

Related Doc. of [ 20348-23-6 ]

Product Details of [ 20348-23-6 ]

Calculated chemistry of [ 20348-23-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 20348-23-6 ]

Application In Synthesis of [ 20348-23-6 ]

[ 20348-23-6 ] Synthesis Path-Upstream 1~7

[ 20348-23-6 ] Synthesis Path-Downstream 1~59

Related Parent Nucleus of [ 20348-23-6 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Parent Nucleus of
[ 20348-23-6 ]