[ CAS No. 142166-01-6 ] {[proInfo.proName]}

Name: 142166-01-6|Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate|97%
Brand: Ambeed
SKU: A362116
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Quality Control of [ 142166-01-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 142166-01-6 ]

CAS No. :	142166-01-6	MDL No. :	MFCD11848180
Formula :	C₁₀H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QHAIQLAFSPRIGM-UHFFFAOYSA-N
M.W :	193.20	Pubchem ID :	18961793
Synonyms :

Calculated chemistry of [ 142166-01-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.34
TPSA :	47.56 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) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	0.71
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	1.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.31 mg/ml ; 0.00679 mol/l
Class :	Soluble
Log S (Ali) :	-2.11
Solubility :	1.51 mg/ml ; 0.00783 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.292 mg/ml ; 0.00151 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Safety of [ 142166-01-6 ]

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 [ 142166-01-6 ]

* 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 [ 142166-01-6 ]
Downstream synthetic route of [ 142166-01-6 ]

[ 142166-01-6 ] Synthesis Path-Upstream 1~9

1
[ 142166-00-5 ]
[ 142166-01-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.333333 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0 - 35℃;	A mixture of methyl 3-oxo-3 , 4-dihydro-2H-l , 4-benzoxazine- 7-carboxylate (1 g, 4.83 mmol) and boron trifluoride ether complex (1.273 mL, 10.14 mmol) in THF (20 mL) was stirred at 0°C for 20 min. To the mixture was. added NaBH₄ (0.383 g, 10.14 mmol), which was stirred at 0°C at 1 h and room temperature overnight. EtOAc (ca. 1 mL) was added, followed by IN HC1 aq. at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na₂SO₄ and concentrated in vacuo to give the title compound (0.916 g, 4.74 mmol,. 98percent) as pale yellow solids.

Reference： [1] Patent: WO2018/30550, 2018, A1, . Location in patent: Paragraph 0658
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248

2
[ 106-93-4 ]
[ 63435-16-5 ]
[ 142166-01-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36 h;	Step 2 Methyl 3,4-dihydro-2H-benzo[b][1, 4]oxazine-7-carboxylate Methyl 4-amino-3-hydroxybenzoate (55 g, 329 mmol) prepared in step 1 and 1,2-dibromoethane (185 g, 986 mmol) were dissolved in DMF (1 L) in a 2 L flask, to which K₂CO₃ (227 g, 1645 mmol) was added, followed by stirring at room temperature for 36 hours. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO₄ and filtered. The solvent was eliminated from the mixture via vacuum distillation, followed by column chromatography to give methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (41.3 g, 213 mmol, 65percent).

Reference： [1] Patent: US2016/355483, 2016, A1, . Location in patent: Paragraph 0331-0332
[2] Patent: CN108276382, 2018, A, . Location in patent: Paragraph 0379; 0381; 0382; 0383

3
[ 156578-96-0 ]
[ 142166-01-6 ]

Reference： [1] Patent: WO2005/39572, 2005, A1, . Location in patent: Page/Page column 33

4
[ 138035-71-9 ]
[ 142166-01-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248

5
[ 619-14-7 ]
[ 142166-01-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248

6
[ 713-52-0 ]
[ 142166-01-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248

7
[ 2374-03-0 ]
[ 142166-01-6 ]

Reference： [1] Patent: US2016/355483, 2016, A1,

8
[ 63435-16-5 ]
[ 142166-01-6 ]

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

9
[ 142166-01-6 ]
[ 851202-96-5 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: With sodium hydroxide In methanol; water at 60℃; for 48 h; Stage #2: With hydrogenchloride In water	3, 4-Dihydro-2H-benzo [1, 4] oxazine-7-carboxylic acid methyl ester (52 mmol) was dissolved in MeOH (20 mL) and NaOH (2M) (20 mL) and stirred at 60 °C for 48h. The organic solvent was removed by evaporation, and the aqueous phase acidified with HC1 (4M). The organic products separated as an oil, and were extracted with ethyl acetate. The organic extract was dried over MgS04, filtered and evaporated. The crude was purified by flash chromatography on silica with gradient elution (heptane/ethyl acetate). Yield: 31 percent 1H NMR (D6-DMSO) : 3.33 (t, 2H); 4.10 (t, 2H); 6.51 (d, 1H); 7.16 (d, 1H); 7.30 (dd, 1H).
1.2 g	With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 12 h;	Step 3: 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (1 g, 5.2 mmol) was dissolved in MeOH (5 ml) and THF (10 ml) in a 25 mL flask, to which LiOH (2 g) dissolved in H₂O (5 ml) was added, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, the solvent was concentrated. The pH of the reaction mixture was adjusted to 5 by using 2N HCl. The mixture was extracted with EA. The organic layer was dried over MgSO₄ and filtered. As a result, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid was obtained (1.2 g).

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Patent: WO2005/39572, 2005, A1, . Location in patent: Page/Page column 33
[3] Patent: US2016/355483, 2016, A1, . Location in patent: Paragraph 0382-0383

[ 142166-01-6 ] Synthesis Path-Downstream 1~51

1
[ 142166-01-6 ]
[ 851202-96-5 ]

Yield	Reaction Conditions	Operation in experiment
31%		3, 4-Dihydro-2H-benzo [1, 4] oxazine-7-carboxylic acid methyl ester (52 mmol) was dissolved in MeOH (20 mL) and NaOH (2M) (20 mL) and stirred at 60 C for 48h. The organic solvent was removed by evaporation, and the aqueous phase acidified with HC1 (4M). The organic products separated as an oil, and were extracted with ethyl acetate. The organic extract was dried over MgS04, filtered and evaporated. The crude was purified by flash chromatography on silica with gradient elution (heptane/ethyl acetate). Yield: 31 % 1H NMR (D6-DMSO) : 3.33 (t, 2H); 4.10 (t, 2H); 6.51 (d, 1H); 7.16 (d, 1H); 7.30 (dd, 1H).
1.2 g	With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 12.0h;	Step 3: 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (1 g, 5.2 mmol) was dissolved in MeOH (5 ml) and THF (10 ml) in a 25 mL flask, to which LiOH (2 g) dissolved in H2O (5 ml) was added, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, the solvent was concentrated. The pH of the reaction mixture was adjusted to 5 by using 2N HCl. The mixture was extracted with EA. The organic layer was dried over MgSO4 and filtered. As a result, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid was obtained (1.2 g).

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248
[2]Patent: WO2005/39572,2005,A1 .Location in patent: Page/Page column 33
[3]Patent: US2016/355483,2016,A1 .Location in patent: Paragraph 0382-0383

2
[ 142166-00-5 ]
[ 142166-01-6 ]

Yield	Reaction Conditions	Operation in experiment
98%		A mixture of methyl 3-oxo-3 , 4-dihydro-2H-l , 4-benzoxazine- 7-carboxylate (1 g, 4.83 mmol) and boron trifluoride ether complex (1.273 mL, 10.14 mmol) in THF (20 mL) was stirred at 0C for 20 min. To the mixture was. added NaBH4 (0.383 g, 10.14 mmol), which was stirred at 0C at 1 h and room temperature overnight. EtOAc (ca. 1 mL) was added, followed by IN HC1 aq. at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (0.916 g, 4.74 mmol,. 98%) as pale yellow solids.

Reference： [1]Patent: WO2018/30550,2018,A1 .Location in patent: Paragraph 0658
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

3
[ 142166-01-6 ]
3,4-dihydro-2<i>H</i>-benzo[1,4]oxazine-7-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

4
4-amino-3-methoxycarbonylmethoxy-benzoic acid methyl ester [ No CAS ]
[ 142166-01-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

5
[ 138035-71-9 ]
[ 142166-01-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

6
[ 619-14-7 ]
[ 142166-01-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

7
[ 713-52-0 ]
[ 142166-01-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8219 - 8248

8
[ 156578-96-0 ]
[ 142166-01-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 96.0h;	4-Amino-3- (2-chloro-ethoxy)-benzoic acid methyl ester (58 mmol) was dissolved in DMF (150 mL) and K2CO3 (60 mmol) was added. Stirred at 100C for 4 days. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate. The organic phases were washed with NH4C1 (sat. ), dried over MgS04, filtered and evaporated. The crude product was used directly in the next reaction.

Reference： [1]Patent: WO2005/39572,2005,A1 .Location in patent: Page/Page column 33

Yield	Reaction Conditions	Operation in experiment
		Reference Example 47 Synthesis of methyl 3,4-dihydro-2H-1,4-benzoxazin-7carboxylate Under nitrogen atmosphere, to tetrahydrofuran (30 ml) were added tetrahydrofuran.borane complex (1[M] solution, 10 ml) and the compound (440 mg) of Reference example 46 at 0 C., and the mixture was stirred at room temperature for 15 minutes, and then reflexed for 4 hours. The reaction mixture was cooled to room temperature and 6N-hydrochloric acid (2.7 ml) was added thereto. The reaction mixture was condensed under reduced pressure and poured into water and made alkaline with 2N-sodium hydroxide aqueous solution. Then, the title compound was extracted with ethyl acetate and the organic layer obtained was washed with a saline solution and dried over magnesium sulfate. After removing the solvent under reduced pressure, the residue obtained was subjected to silica gel column chromatography. The residue was developed and eluted with a mixed solvent of hexane:ethyl acetate=3:2 to obtain the title compound (310 mg). 1 H-NMR (CDCl3: delta): 3.46 (2H, m), 3.84 (3H, s), 4.22 (2H, t, J=4.4 Hz), 4.30 (1H, m), 6.53 (1H, d, J=9.8 Hz), 7.45 (1H, s), 7.47 (1H, d, J=9.8 Hz).

10
[ 142166-01-6 ]
[ 144-55-8 ]
methyl 4-[(2,4-diamino-6-pteridinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; ISOPROPYLAMIDE;	Reference Example 42 Synthesis of methyl 4-[(2,4-diamino-6-pteridinyl)methyl]-3,4 -dihydro-2H-1,4-benzoxazin-7-carboxylate In dimethylacetamide (10 ml) were suspended 6-bromomethyl-2,4-diaminopteridine hydrobromide.isopropanol adduct (410 mg) and <strong>[142166-01-6]methyl 3,4-dihydro-2H-1,4-benzoxazin-7-carboxylate</strong> (200 mg), and the suspension was stirred at a bath temperature of 65 C. for 4 hours and at 90 C. for 19 hours. After cooling, dimethylacetamide was condensed under reduced pressure, and chloroform and an aqueous sodium hydrogen carbonate solution were added to the condensate. After precipitates were filtered off, the organic layer was washed with water and dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel chromatography and eluted by using a mixed solvent of chloroform:methanol=97:3 to obtain the title compound (100 mg). 1 H-NMR (CDCl3:CD3 OD=9:1, delta): 3.63 (2H, brt), 3.84 (3H, s), 4.32 (2H, brt), 4.72 (2H, s), 6.68 (1H, d, J=9.0 Hz), 7.47 (1H, s), 7.50 (1H, d, J=9.0 Hz), 8.71 (1H, s).

Reference： [1]Patent: US5354753,1994,A

11
[ 142166-01-6 ]
[ 1223463-12-4 ]
methyl 4-((2'-(tert-butoxycarbonyl)-2-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1, 4]oxazine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.4 g	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 12.0h;	Step 4: methyl 4-((2'-(tert-butoxycarbonyl)-2-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1, 4]oxazine-7-carboxylate Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (10 g, 51.7 mmol) was dissolved in DMF (50 ml) in a 250 mL flask, to which NaH (6.2 g, 155.3 mmol) and tert-butyl 4'-(bromomethyl)-2'-fluoro-[1,1'-biphenyl]-2-carboxylate (2.5 g, 67.3 mmol) were added, followed by stirring at room temperature for 12 hours. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO4 and filtered. The solvent was eliminated from the mixture via vacuum distillation, followed by column chromatography to give methyl 4-((2'-(tert-butoxycarbonyl)-2-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (15.4 g).

Reference： [1]Patent: US2016/355483,2016,A1 .Location in patent: Paragraph 0394-0395

12
[ 142166-01-6 ]
4-((2'-(tert-butoxycarbonyl)-2-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

13
[ 142166-01-6 ]
(S)-2'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-4-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

14
[ 142166-01-6 ]
(S)-4-((4'-carbamoyl-[1,1'-biphenyl]-2-yl)methyl)-N-(1-phenylethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

15
[ 142166-01-6 ]
[ 114772-40-6 ]
methyl 4-((2'-(tert-butoxycarbonyl)-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 12.0h;	Step 3 Methyl 4-((2'-(tert-butoxycarbonyl)-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (8.08 g, 41.8 mmol) obtained in step 2 was dissolved in DMF (50 ml) in a 500 mL flask, to which NaH (2 g, 50.2 mmol) and tert-butyl 4'-(bromomethyl)-[1,1'-biphenyl]-2-carboxylate (17.4 g, 50.2 mmol) were added, followed by stirring at room temperature for 12 hours. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO4 and filtered. The solvent was eliminated from the mixture via vacuum distillation, followed by column chromatography to give methyl 4-((2'-(tert-butoxycarbonyl)-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (28.4 g, 68.03 mmol, 68%).

Reference： [1]Patent: US2016/355483,2016,A1 .Location in patent: Paragraph 0333-0334

16
[ 106-93-4 ]
[ 63435-16-5 ]
[ 142166-01-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 36h;	Step 2 Methyl 3,4-dihydro-2H-benzo[b][1, 4]oxazine-7-carboxylate Methyl 4-amino-3-hydroxybenzoate (55 g, 329 mmol) prepared in step 1 and 1,2-dibromoethane (185 g, 986 mmol) were dissolved in DMF (1 L) in a 2 L flask, to which K2CO3 (227 g, 1645 mmol) was added, followed by stirring at room temperature for 36 hours. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO4 and filtered. The solvent was eliminated from the mixture via vacuum distillation, followed by column chromatography to give methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (41.3 g, 213 mmol, 65%).
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h;	At room temperature,Methyl 4-amino-3-hydroxybenzoate (2.10 g, 12.7 mmol), potassium carbonate (7.10 g, 50.8 mmol), N,N-dimethylformamide (43 mL). 1,2-Dibromoethane (9.65 g, 50.8 mmol) was added, and the mixture was stirred at 80 C for 16 hours. Thin layer chromatography was used to detect the disappearance of most of the starting materials, and then cooled to room temperature, and the insoluble salts were removed by filtration. It was diluted with 30 mL of water and extracted with ethyl acetate (25 mL×3). After concentrating the organic phase, column chromatography gave the title compound.

Reference： [1]Patent: US2016/355483,2016,A1 .Location in patent: Paragraph 0331-0332
[2]Patent: CN108276382,2018,A .Location in patent: Paragraph 0379; 0381; 0382; 0383

17
[ 2374-03-0 ]
[ 142166-01-6 ]

Reference： [1]Patent: US2016/355483,2016,A1

18
[ 142166-01-6 ]
4-((2'-(tert-butoxycarbonyl)-[1,1'-biphenyl]-4-yl)methyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

19
[ 142166-01-6 ]
(S)-4'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]2-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

20
[ 142166-01-6 ]
(S)-tert-butyl 4'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

21
[ 142166-01-6 ]
(S)-4-((2'-carbamoyl-[1,1'-biphenyl]-4-yl)methyl)-N-(1-phenylethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxamide [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

22
[ 142166-01-6 ]
sodium (S)-4'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

23
[ 142166-01-6 ]
(S)-methyl 2'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

24
[ 142166-01-6 ]
(S)-tert-butyl 2'-fluoro-4'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

25
[ 142166-01-6 ]
(S)-2'-fluoro-4'-((7-((1-phenylethyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2016/355483,2016,A1

26
[ 142166-01-6 ]
[ 24424-99-5 ]
4-tert-butyl 7-methyl 2,3-dihydro-4H-1,4-benzoxazine-4,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.7%	With dmap; triethylamine; In tetrahydrofuran; at 50℃; for 3.0h;	A mixture of methyl 3, 4-dihydro-2H-l, 4-benzoxazine-7- carboxylate (10.07 g, 52.13 mmol), Boc20 (14:52 mL, 62.56 mraol), TEA (8.72 mL, 62.56 mmol) and DMAP (3.18 g, 26.07 mmol) in THF (200 mL) was stirred at 50C for 3 h. The mixture was quenched with brine at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over (3718) MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%- 30% EtOAc in hexane) to give the title compound (9.90 g, 33.8 mmol, 64.7%) as white solids.

Reference： [1]Patent: WO2018/30550,2018,A1 .Location in patent: Paragraph 0674

27
[ 63435-16-5 ]
[ 142166-01-6 ]